Colorant compounds

ABSTRACT

Compounds of the formula 
                         
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 66 , m, n, p, and G are as defined herein.

This application is a divisional of U.S. application Ser. No.10/918,053, filed Aug. 13, 2004, the disclosure of which is totallyincorporated herein by reference.

CROSS-REFERENCE TO RELATED APPLICATIONS

Copending Application U.S. Ser. No. 10/902,594, filed Jul. 29, 2004,entitled “Colorant Compounds,” with the named inventors Jeffery H.Banning, Wolfgang G. Wedler, and C. Wayne Jaeger, the disclosure ofwhich is totally incorporated herein by reference, discloses a colorantcompound of the formula

wherein Y is a hydrogen atom or a bromine atom, n is an integer of 0, 1,2, 3, or 4, R₁ is an alkylene group, an arylene group, an arylalkylenegroup, or an alkylarylene group, provided that no oxygen atom creates a

linkage, X is —O— or —NR₃— wherein R₃ is a hydrogen atom, an alkylgroup, an aryl group, an arylalkyl group, or an alkylaryl group, and R₂is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group,or an alkylaryl group.

Copending Application U.S. Ser. No. 10/902,602, filed Jul. 29, 2004,entitled “Phase Change Inks,” with the named inventors Jeffery H.Banning, Wolfgang G. Wedler, and C. Wayne Jaeger, the disclosure ofwhich is totally incorporated herein by reference, discloses a phasechange ink composition comprising a phase change ink carrier and acolorant compound of the formula

wherein Y is a hydrogen atom or a bromine atom, n is an integer of 0, 1,2, 3, or 4, R₁ is an alkylene group, an arylene group, an arylalkylenegroup, or an alkylarylene group, provided that no oxygen atom creates a

linkage, X is —O— or —NR₃— wherein R₃ is a hydrogen atom, an alkylgroup, an aryl group, an arylalkyl group, or an alkylaryl group, and R₂is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group,or an alkylaryl group.

BACKGROUND

Disclosed herein are colorant compounds. More specifically, disclosedherein are colorant compounds particularly suitable for use in hot meltor phase change inks.

Colorant compounds are disclosed in, for example, U.S. Pat. Nos.6,958,406, 6,821,327, 7,053,227, and 7,211,131, the disclosures of eachof which are totally incorporated herein by reference.

While known compositions and processes are suitable for their intendedpurposes, a need remains for improved colorant compounds. In addition, aneed remains for colorant compositions particularly suitable for use inphase change inks. Further, a need remains for colorant compounds with adesirable magenta color. Additionally, a need remains for colorantcompounds with desirable thermal stability. There is also a need forcolorant compounds with good lightfastness. In addition, there is a needfor colorant compounds that exhibit desirable solubility characteristicsin phase change ink carrier compositions. Further, there is a need forcolorant compounds that, when incorporated into phase change inks,exhibit reduced migration within a layer of printed ink. Additionally,there is a need for colorant compounds that, when incorporated intophase change inks, exhibit reduced crystallization within a layer ofprinted ink. A need also remains for colorant compounds that, whenincorporated into phase change inks, enable production of prints thatmaintain uniform color over long periods of time without unevenness orblotching. In addition, a need remains for colorant compounds that, whenincorporated into phase change inks, enable production of prints thatretain their original color over long periods of time. Further, a needremains for colorant compounds that, when incorporated into phase changeinks, enable production of prints that exhibit reduced sensitivity toimage discoloration upon contact with human fingertips. Additionally, aneed remains for colorant compounds that can be incorporated into phasechange inks in desirably high concentrations. There is also a need forcolorant compounds that can be manufactured easily and practically.

SUMMARY

Disclosed herein are compounds (a) of the formula

wherein R₁ is (i) a hydrogen atom, (ii) an alkyl group, (iii) an arylgroup, (iv) an arylalkyl group, or (v) an alkylaryl group, R₂ is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, (v) an alkylaryl group, or (vi) a substituent otherthan an alkyl, aryl, arylalkyl, or alkylaryl group, R₃ is (i) an alkylgroup, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylarylgroup, or (v) a substituent other than an alkyl, aryl, arylalkyl, oralkylaryl group, m is an integer of 0, 1, 2, 3, or 4, R₄ is (i) an alkylgroup, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylarylgroup, or (v) a substituent other than an alkyl, aryl, arylalkyl, oralkylaryl group, n is an integer of 0, 1, 2, 3, or 4, R₆₆ is (i) analkylene group, (ii) an arylene group, (iii) an arylalkylene group, or(iv) an alkylarylene group, G is (1) a hydroxy group, (2) a carboxylicacid group, (3) an alkyl group having at least about 8 carbon atoms, (4)an aryl group, (5) an arylalkyl group, (6) an alkylaryl group, (7) agroup of the formula

(8) a group of the formula

(9) a group of the formula

or (10) a group of the formula

R₇ is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group,or (iv) an alkylaryl group, R₈ is (i) a hydrogen atom, (ii) an alkylgroup, (iii) an aryl group, (iv) an arylalkyl group, or (v) an alkylarylgroup, X is —O— or —NR₉—, and R₉ is (i) a hydrogen atom, (ii) an alkylgroup, (iii) an aryl group, (iv) an arylalkyl group, or (v) an alkylarylgroup; (b) of the formula

wherein R₁ is (i) a hydrogen atom, (ii) an alkyl group, (iii) an arylgroup, (iv) an arylalkyl group, or (v) an alkylaryl group, R₂ is anitrile group, R₃ is (i) an alkyl group, (ii) an aryl group, (iii) anarylalkyl group, (iv) an alkylaryl group, or (v) a substituent otherthan an alkyl, aryl, arylalkyl, or alkylaryl group, m is an integer of0, 1, 2, 3, or 4, R₄ is (i) an alkyl group, (ii) an aryl group, (iii) anarylalkyl group, (iv) an alkylaryl group, or (v) a substituent otherthan an alkyl, aryl, arylalkyl, or alkylaryl group, n is an integer of0, 1, 2, 3, or 4, R₅ is (i) an alkyl group, (ii) an aryl group, (iii) anarylalkyl group, (iv) an alkylaryl group, or (v) a substituent otherthan an alkyl, aryl, arylalkyl, or alkylaryl group, p is an integer of0, 1, 2, 3, or 4, R₆ is (i) a direct bond, (ii) an alkylene group, (iii)an arylene group, (iv) an arylalkylene group, or (v) an alkylarylenegroup, G is (1) an alkyl group having at least about 14 carbon atoms,(2) an aryl group having at least about 14 carbon atoms, (3) anarylalkyl group having at least about 14 carbon atoms, (4) an alkylarylgroup having at least about 14 carbon atoms, (5) a group of the formula

(6) a group of the formula

(7) a group of the formula

or (8) a group of the formula

R₇ is (i) an alkyl group having at least about 14 carbon atoms, (ii) anaryl group having at least about 14 carbon atoms, (iii) an arylalkylgroup having at least about 14 carbon atoms, or (iv) an alkylaryl grouphaving at least about 14 carbon atoms, R₈ is (i) a hydrogen atom, (ii)an alkyl group, (iii) an aryl group, (iv) an arylalkyl group, or (v) analkylaryl group, X is —O— or —NR₉—, and R₉ is (i) a hydrogen atom, (ii)an alkyl group, (iii) an aryl group, (iv) an arylalkyl group, or (v) analkylaryl group; or (c) of the formula

wherein R₁ is (i) a hydrogen atom, (ii) an alkyl group, (iii) an arylgroup, (iv) an arylalkyl group, or (v) an alkylaryl group, R₂ is (i) ahydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, (v) an alkylaryl group, or (vi) a substituent otherthan an alkyl, aryl, arylalkyl, alkylaryl, or nitrile group, R₃ is (i)an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) analkylaryl group, or (v) a substituent other than an alkyl, aryl,arylalkyl, or alkylaryl group, m is an integer of 0, 1, 2, 3, or 4, R₄is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group,(iv) an alkylaryl group, or (v) a substituent other than an alkyl, aryl,arylalkyl, or alkylaryl group, n is an integer of 0, 1, 2, 3, or 4, R₅is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group,(iv) an alkylaryl group, or (v) a substituent other than an alkyl, aryl,arylalkyl, or alkylaryl group, p is an integer of 0, 1, 2, 3, or 4, R₆is (i) a direct bond, (ii) an alkylene group, (iii) an arylene group,(iv) an arylalkylene group, or (v) an alkylarylene group, G is (1) ahydroxy group, (2) a carboxylic acid group, (3) an alkyl group having atleast about 8 carbon atoms, (4) an aryl group, (5) an arylalkyl group,(6) an alkylaryl group, (7) a group of the formula

(8) a group of the formula

(9) a group of the formula

or (10) a group of the formula

R₇ is (i) an alkyl group having at least about 8 carbon atoms, (ii) anaryl group, (iii) an arylalkyl group, or (iv) an alkylaryl group, R₈ is(i) a hydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group, X is —O— or —NR₉—, and R₉ is(i) a hydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) anarylalkyl group, or (v) an alkylaryl group.

DETAILED DESCRIPTION

The compounds disclosed herein are of the general formula

In these compounds, R₁ is (i) a hydrogen atom, (ii) an alkyl group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the alkyl group), in one embodimentwith at least about 1 carbon atom, and in one embodiment with no morethan about 50 carbon atoms, in another embodiment with no more thanabout 18 carbon atoms, and in yet another embodiment with no more thanabout 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (iii) an aryl group (including substituted andunsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about5 carbon atoms, and in another embodiment with at least about 6 carbonatoms, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, and in yetanother embodiment with no more than about 12 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in either thearyl or the alkyl portion of the arylalkyl group), in one embodimentwith at least about 6 carbon atoms, and in another embodiment with atleast about 7 carbon atoms, and in one embodiment with no more thanabout 50 carbon atoms, in another embodiment with no more than about 18carbon atoms, and in yet another embodiment with no more than about 12carbon atoms, although the number of carbon atoms can be outside ofthese ranges, such as benzyl or the like, or (v) an alkylaryl group(including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like, with specific examples of R₁ groups including (butnot being limited to) a hydrogen atom, a methyl group, and the like.

In the compounds of the formula

R₂ is (i) a hydrogen atom, (ii) an alkyl group (including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms, such as oxygen, nitrogen,sulfur, silicon, phosphorus, and the like either may or may not bepresent in the alkyl group), in one embodiment with at least about 1carbon atom, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges,(iii) an aryl group (including substituted and unsubstituted arylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe aryl group), in one embodiment with at least about 5 carbon atoms,and in another embodiment with at least about 6 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (iv) an arylalkyl group(including substituted and unsubstituted arylalkyl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the aryl or thealkyl portion of the arylalkyl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas benzyl or the like, (v) an alkylaryl group (including substituted andunsubstituted alkylaryl groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the alkyl or the aryl portion of thealkylaryl group), in one embodiment with at least about 6 carbon atoms,and in another embodiment with at least about 7 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolyl or thelike, or (vi) a substituent other than an alkyl, aryl, arylalkyl, oralkylaryl group, including (but not limited to) hydroxy groups, halogenatoms, amine groups, imine groups, ammonium groups, cyano groups,pyridine groups, pyridinium groups, ether groups, aldehyde groups,ketone groups, ester groups, amide groups, carbonyl groups, thiocarbonylgroups, sulfate groups, sulfonate groups, sulfonic acid groups, sulfidegroups, sulfoxide groups, phosphine groups, phosphonium groups,phosphate groups, nitrile groups, mercapto groups, nitro groups, nitrosogroups, sulfone groups, acyl groups, acid anhydride groups, azidegroups, azo groups, cyanato groups, isocyanato groups, thiocyanatogroups, isothiocyanato groups, carboxylate groups, carboxylic acidgroups, urethane groups, urea groups, mixtures thereof, and the like,wherein two or more substituents can be joined together to form a ring,with some specific examples of R₂ groups including (but not beinglimited to) —H, —CN, a phenyl group (—C₆H₅), an ester group of theformula —C(═O)OR₈₈ wherein R₈₈ is an alkyl group, such as methyl, ethyl,propyl, or the like, and the like.

In the compounds of the formula

in one embodiment, R₂ is a nitrile group (—CN). In another embodiment,R₂ is (i) a hydrogen atom, (ii) an alkyl group (including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms, such as oxygen, nitrogen,sulfur, silicon, phosphorus, and the like either may or may not bepresent in the alkyl group), in one embodiment with at least about 1carbon atom, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges,(iii) an aryl group (including substituted and unsubstituted arylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe aryl group), in one embodiment with at least about 5 carbon atoms,and in another embodiment with at least about 6 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (iv) an arylalkyl group(including substituted and unsubstituted arylalkyl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the aryl or thealkyl portion of the arylalkyl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas benzyl or the like, (v) an alkylaryl group (including substituted andunsubstituted alkylaryl groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the alkyl or the aryl portion of thealkylaryl group), in one embodiment with at least about 6 carbon atoms,and in another embodiment with at least about 7 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolyl or thelike, or (vi) a substituent other than an alkyl, aryl, arylalkyl,alkylaryl, or nitrile group, including (but not limited to) hydroxygroups, halogen atoms, amine groups, imine groups, ammonium groups,pyridine groups, pyridinium groups, ether groups, aldehyde groups,ketone groups, ester groups, amide groups, carbonyl groups, thiocarbonylgroups, sulfate groups, sulfonate groups, sulfonic acid groups, sulfidegroups, sulfoxide groups, phosphine groups, phosphonium groups,phosphate groups, mercapto groups, nitro groups, nitroso groups, sulfonegroups, acyl groups, acid anhydride groups, azide groups, azo groups,cyanato groups, isocyanato groups, thiocyanato groups, isothiocyanatogroups, carboxylate groups, carboxylic acid groups, urethane groups,urea groups, mixtures thereof, and the like, wherein two or moresubstituents can be joined together to form a ring, with some specificexamples of R₂ groups including (but not being limited to) —H, a phenylgroup (—C₆H₅), an ester group of the formula —C(═O)OR₈₈ wherein R₈₈ isan alkyl group, such as methyl, ethyl, propyl, or the like, and thelike.

In the compounds of the formulae

R₃ is (i) an alkyl group (including linear, branched, saturated,unsaturated, cyclic, substituted, and unsubstituted alkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in the alkylgroup), in one embodiment with at least about 1 carbon atom, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (ii) an aryl group(including substituted and unsubstituted aryl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the aryl group), in oneembodiment with at least about 5 carbon atoms, and in another embodimentwith at least about 6 carbon atoms, and in one embodiment with no morethan about 50 carbon atoms, in another embodiment with no more thanabout 18 carbon atoms, and in yet another embodiment with no more thanabout 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (iii) an arylalkyl group (including substitutedand unsubstituted arylalkyl groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the aryl or the alkyl portion of thearylalkyl group), in one embodiment with at least about 6 carbon atoms,and in another embodiment with at least about 7 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as benzyl or thelike, (iv) an alkylaryl group (including substituted and unsubstitutedalkylaryl groups, and wherein hetero atoms, such as oxygen, nitrogen,sulfur, silicon, phosphorus, and the like either may or may not bepresent in either the alkyl or the aryl portion of the alkylaryl group),in one embodiment with at least about 6 carbon atoms, and in anotherembodiment with at least about 7 carbon atoms, and in one embodimentwith no more than about 50 carbon atoms, in another embodiment with nomore than about 18 carbon atoms, and in yet another embodiment with nomore than about 12 carbon atoms, although the number of carbon atoms canbe outside of these ranges, such as tolyl or the like, or (v) asubstituent other than an alkyl, aryl, arylalkyl, or alkylaryl group,including (but not limited to) hydroxy groups, halogen atoms, aminegroups, imine groups, ammonium groups, cyano groups, pyridine groups,pyridinium groups, ether groups, aldehyde groups, ketone groups, estergroups, amide groups, carbonyl groups, thiocarbonyl groups, sulfategroups, sulfonate groups, sulfonic acid groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, mixtures thereof, and the like, whereintwo or more substituents can be joined together to form a ring, m is aninteger of 0, 1, 2, 3, or 4, R₄ is (i) an alkyl group (including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms, such as oxygen, nitrogen,sulfur, silicon, phosphorus, and the like either may or may not bepresent in the alkyl group), in one embodiment with at least about 1carbon atom, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, (ii)an aryl group (including substituted and unsubstituted aryl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in the arylgroup), in one embodiment with at least about 5 carbon atoms, and inanother embodiment with at least about 6 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (iii) an arylalkyl group(including substituted and unsubstituted arylalkyl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the aryl or thealkyl portion of the arylalkyl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas benzyl or the like, (iv) an alkylaryl group (including substitutedand unsubstituted alkylaryl groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the alkyl or the aryl portion of thealkylaryl group), in one embodiment with at least about 6 carbon atoms,and in another embodiment with at least about 7 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolyl or thelike, or (v) a substituent other than an alkyl, aryl, arylalkyl, oralkylaryl group, including (but not limited to) hydroxy groups, halogenatoms, amine groups, imine groups, ammonium groups, cyano groups,pyridine groups, pyridinium groups, ether groups, aldehyde groups,ketone groups, ester groups, amide groups, carbonyl groups, thiocarbonylgroups, sulfate groups, sulfonate groups, sulfonic acid groups, sulfidegroups, sulfoxide groups, phosphine groups, phosphonium groups,phosphate groups, nitrile groups, mercapto groups, nitro groups, nitrosogroups, sulfone groups, acyl groups, acid anhydride groups, azidegroups, azo groups, cyanato groups, isocyanato groups, thiocyanatogroups, isothiocyanato groups, carboxylate groups, carboxylic acidgroups, urethane groups, urea groups, mixtures thereof, and the like,wherein two or more substituents can be joined together to form a ring,n is an integer of 0, 1, 2, 3, or 4, R₅ is (i) an alkyl group (includinglinear, branched, saturated, unsaturated, cyclic, substituted, andunsubstituted alkyl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the alkyl group), in one embodiment with at leastabout 1 carbon atom, and in one embodiment with no more than about 50carbon atoms, in another embodiment with no more than about 18 carbonatoms, and in yet another embodiment with no more than about 12 carbonatoms, although the number of carbon atoms can be outside of theseranges, (ii) an aryl group (including substituted and unsubstituted arylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe aryl group), in one embodiment with at least about 5 carbon atoms,and in another embodiment with at least about 6 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (iii) an arylalkyl group(including substituted and unsubstituted arylalkyl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the aryl or thealkyl portion of the arylalkyl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas benzyl or the like, (iv) an alkylaryl group (including substitutedand unsubstituted alkylaryl groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the alkyl or the aryl portion of thealkylaryl group), in one embodiment with at least about 6 carbon atoms,and in another embodiment with at least about 7 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolyl or thelike, or (v) a substituent other than an alkyl, aryl, arylalkyl, oralkylaryl group, including (but not limited to) hydroxy groups, halogenatoms, amine groups, imine groups, ammonium groups, cyano groups,pyridine groups, pyridinium groups, ether groups, aldehyde groups,ketone groups, ester groups, amide groups, carbonyl groups, thiocarbonylgroups, sulfate groups, sulfonate groups, sulfonic acid groups, sulfidegroups, sulfoxide groups, phosphine groups, phosphonium groups,phosphate groups, nitrile groups, mercapto groups, nitro groups, nitrosogroups, sulfone groups, acyl groups, acid anhydride groups, azidegroups, azo groups, cyanato groups, isocyanato groups, thiocyanatogroups, isothiocyanato groups, carboxylate groups, carboxylic acidgroups, urethane groups, urea groups, mixtures thereof, and the like,wherein two or more substituents can be joined together to form a ring,p is an integer of 0, 1, 2, 3, or 4, R₆ is (i) a direct bond (i.e., R₆can be missing entirely and the G group can be directly bonded to thearomatic ring), (ii) an alkylene group (including linear, branched,saturated, unsaturated, cyclic, substituted, and unsubstituted alkylenegroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe alkylene group), in one embodiment with at least about 1 carbonatom, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, in yetanother embodiment with no more than about 12 carbon atoms, in stillanother embodiment with no more than about 2 carbon atoms, and inanother embodiment with exactly 1 carbon atom, although the number ofcarbon atoms can be outside of these ranges, (iii) an arylene group(including unsubstituted and substituted arylene groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in the arylene group), in oneembodiment with at least about 5 carbon atoms, and in another embodimentwith at least about 6 carbon atoms, and in one embodiment with no morethan about 50 carbon atoms, in another embodiment with no more thanabout 18 carbon atoms, in yet another embodiment with no more than about12 carbon atoms, although the number of carbon atoms can be outside ofthese ranges, (iv) an arylalkylene group (including unsubstituted andsubstituted arylalkylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the aryl and the alkylportions of the arylalkylene group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms, inyet another embodiment with no more than about 12 carbon atoms, althoughthe number of carbon atoms can be outside of these ranges, such asbenzyl or the like, including (a) arylalkylene groups wherein both thearyl and the alkyl portions form the linkage between the

moiety and the-Gmoiety, such as

and the like, and (b) arylalkylene groups wherein only the alkyl portionforms the linkage between the

moiety and the-Gmoiety and the alkyl portion has aryl portions pending therefrom, suchas

and the like, or (v) an alkylarylene group (including unsubstituted andsubstituted alkylarylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the aryl and the alkylportions of the alkylarylene group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms, inyet another embodiment with no more than about 12 carbon atoms, althoughthe number of carbon atoms can be outside of these ranges, such astolyl, phenylethyl, or the like, including (a) alkylarylene groupswherein both the aryl and the alkyl portions form the linkage betweenthe

moiety and the-Gmoiety, such as

and the like, and (b) alkylarylene groups wherein only the aryl portionforms the linkage between the

moiety and the-Gmoiety and the aryl portion has alkyl portions pending therefrom, suchas

and the like, with specific examples of R₆ including (but not beinglimited to) —CH₂—, —CH₂CH₂—, and the like, R₆₆ is (i) an alkylene group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkylene groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the alkylene group), in oneembodiment with at least about 1 carbon atom, and in one embodiment withno more than about 50 carbon atoms, in another embodiment with no morethan about 18 carbon atoms, in yet another embodiment with no more thanabout 12 carbon atoms, in still another embodiment with no more thanabout 2 carbon atoms, and in another embodiment with exactly 1 carbonatom, although the number of carbon atoms can be outside of theseranges, (ii) an arylene group (including unsubstituted and substitutedarylene groups, and wherein hetero atoms, such as oxygen, nitrogen,sulfur, silicon, phosphorus, and the like either may or may not bepresent in the arylene group), in one embodiment with at least about 5carbon atoms, and in another embodiment with at least about 6 carbonatoms, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, in yetanother embodiment with no more than about 12 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iii) anarylalkylene group (including unsubstituted and substituted arylalkylenegroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present ineither or both of the aryl and the alkyl portions of the arylalkylenegroup), in one embodiment with at least about 6 carbon atoms, and inanother embodiment with at least about 7 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as benzyl or thelike, including (a) arylalkylene groups wherein both the aryl and thealkyl portions form the linkage between the

moiety and the-Gmoiety, such as

and the like, and (b) arylalkylene groups wherein only the alkyl portionforms the linkage between the

moiety and the-Gmoiety and the alkyl portion has aryl portions pending therefrom, suchas

and the like, or (iv) an alkylarylene group (including unsubstituted andsubstituted alkylarylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the aryl and the alkylportions of the alkylarylene group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms, inyet another embodiment with no more than about 12 carbon atoms, althoughthe number of carbon atoms can be outside of these ranges, such astolyl, phenylethyl, or the like, including (a) alkylarylene groupswherein both the aryl and the alkyl portions form the linkage betweenthe

moiety and the-Gmoiety, such as

and the like, and (b) alkylarylene groups wherein only the aryl portionforms the linkage between the

moiety and the-Gmoiety and the aryl portion has alkyl portions pending therefrom, suchas

and the like, with specific examples of R₆₆ including (but not beinglimited to) —CH₂—, —CH₂CH₂—, and the like, G, in various embodiments, is(1) a hydroxy group, (2) a carboxylic acid group, (3) an alkyl group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the alkyl group), in one embodimentwith at least about 8 carbon atoms, in another embodiment with at leastabout 9 carbon atoms, in yet another embodiment with at least about 10carbon atoms, in still another embodiment with at least about 11 carbonatoms, in another embodiment with at least about 12 carbon atoms, in yetanother embodiment with at least about 13 carbon atoms, in still anotherembodiment with at least about 14 carbon atoms, in another embodimentwith at least about 15 carbon atoms, in yet another embodiment with atleast about 16 carbon atoms, in still another embodiment with at leastabout 17 carbon atoms, in another embodiment with at least about 18carbon atoms, in yet another embodiment with at least about 19 carbonatoms, and in still another embodiment with at least about 20 carbonatoms, and in one embodiment with no more than about 50 carbon atoms,although the number of carbon atoms can be outside of these ranges, (4)an aryl group (including substituted and unsubstituted aryl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in the arylgroup), in one embodiment with at least about 5 carbon atoms, in anotherembodiment with at least about 6 carbon atoms, in yet another embodimentwith at least about 7 carbon atoms, in still another embodiment with atleast about 8 carbon atoms, in another embodiment with at least about 9carbon atoms, in yet another embodiment with at least about 10 carbonatoms, in still another embodiment with at least about 11 carbon atoms,in another embodiment with at least about 12 carbon atoms, in yetanother embodiment with at least about 13 carbon atoms, in still anotherembodiment with at least about 14 carbon atoms, in another embodimentwith at least about 15 carbon atoms, in yet another embodiment with atleast about 16 carbon atoms, in still another embodiment with at leastabout 17 carbon atoms, in another embodiment with at least about 18carbon atoms, in yet another embodiment with at least about 19 carbonatoms, in still another embodiment with at least about 20 carbon atoms,and in one embodiment with no more than about 50 carbon atoms, althoughthe number of carbon atoms can be outside of these ranges, such asbenzyl or the like, (5) an arylalkyl group (including substituted andunsubstituted arylalkyl groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the aryl or the alkyl portion of thearylalkyl group), in one embodiment with at least about 6 carbon atoms,in another embodiment with at least about 7 carbon atoms, in yet anotherembodiment with at least about 8 carbon atoms, in still anotherembodiment with at least about 9 carbon atoms, in another embodimentwith at least about 10 carbon atoms, in yet another embodiment with atleast about 11 carbon atoms, in still another embodiment with at leastabout 12 carbon atoms, in another embodiment with at least about 13carbon atoms, in yet another embodiment with at least about 14 carbonatoms, in another embodiment with at least about 15 carbon atoms, in yetanother embodiment with at least about 16 carbon atoms, in still anotherembodiment with at least about 17 carbon atoms, in another embodimentwith at least about 18 carbon atoms, in yet another embodiment with atleast about 19 carbon atoms, in still another embodiment with at leastabout 20 carbon atoms, in another embodiment with at least about 21carbon atoms, in yet another embodiment with at least about 22 carbonatoms, in still another embodiment with at least about 23 carbon atoms,in another embodiment with at least about 24 carbon atoms, in yetanother embodiment with at least about 25 carbon atoms, and in stillanother embodiment with at least about 26 carbon atoms, and in oneembodiment with no more than about 50 carbon atoms, although the numberof carbon atoms can be outside of these ranges, (6) an alkylaryl group(including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group), in one embodiment with at leastabout 14 carbon atoms, in another embodiment with at least about 15carbon atoms, in yet another embodiment with at least about 16 carbonatoms, in still another embodiment with at least about 17 carbon atoms,in another embodiment with at least about 18 carbon atoms, in yetanother embodiment with at least about 19 carbon atoms, in still anotherembodiment with at least about 20 carbon atoms, in another embodimentwith at least about 21 carbon atoms, in yet another embodiment with atleast about 22 carbon atoms, in still another embodiment with at leastabout 23 carbon atoms, in another embodiment with at least about 24carbon atoms, in yet another embodiment with at least about 25 carbonatoms, and in still another embodiment with at least about 26 carbonatoms, and in one embodiment with no more than about 50 carbon atoms,although the number of carbon atoms can be outside of these ranges, (7)a group of the formula

(8) a group of the formula

(9) a group of the formula

or (10) a group of the formula

R₇ is, in various embodiments, (i) an alkyl group (including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms, such as oxygen, nitrogen,sulfur, silicon, phosphorus, and the like either may or may not bepresent in the alkyl group), in one embodiment with at least about 1carbon atom, in another embodiment at least about 2 carbon atoms, in yetanother embodiment at least about 3 carbon atoms, in still anotherembodiment at least about 4 carbon atoms, in another embodiment at leastabout 5 carbon atoms, in yet another embodiment at least about 6 carbonatoms, in still another embodiment at least about 7 carbon atoms, inanother embodiment with at least about 8 carbon atoms, in anotherembodiment at least about 9 carbon atoms, in yet another embodiment atleast about 10 carbon atoms, in still another embodiment at least about11 carbon atoms, in another embodiment at least about 12 carbon atoms,in yet another embodiment at least about 13 carbon atoms, in stillanother embodiment at least about 14 carbon atoms, in another embodimentat least about 15 carbon atoms, in yet another embodiment at least about16 carbon atoms, in still another embodiment at least about 17 carbonatoms, in another embodiment at least about 18 carbon atoms, in yetanother embodiment at least about 19 carbon atoms, in still anotherembodiment at least about 20 carbon atoms, in another embodiment atleast about 21 carbon atoms, in yet another embodiment at least about 22carbon atoms, in still another embodiment at least about 23 carbonatoms, in another embodiment at least about 24 carbon atoms, in yetanother embodiment at least about 25 carbon atoms, in still anotherembodiment at least about 26 carbon atoms, in another embodiment atleast about 27 carbon atoms, in yet another embodiment at least about 28carbon atoms, in still another embodiment at least about 29 carbonatoms, in another embodiment at least about 30 carbon atoms, in yetanother embodiment at least about 31 carbon atoms, and in still anotherembodiment at least about 32 carbon atoms, and in one embodiment with nomore than about 50 carbon atoms, (ii) an aryl group (includingsubstituted and unsubstituted aryl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the aryl group), in one embodimentwith at least about 5 carbon atoms, in another embodiment with at leastabout 6 carbon atoms, in still another embodiment at least about 7carbon atoms, in another embodiment with at least about 8 carbon atoms,in another embodiment at least about 9 carbon atoms, in yet anotherembodiment at least about 10 carbon atoms, in still another embodimentat least about 11 carbon atoms, in another embodiment at least about 12carbon atoms, in yet another embodiment at least about 13 carbon atoms,in still another embodiment at least about 14 carbon atoms, in anotherembodiment at least about 15 carbon atoms, in yet another embodiment atleast about 16 carbon atoms, in still another embodiment at least about17 carbon atoms, in another embodiment at least about 18 carbon atoms,in yet another embodiment at least about 19 carbon atoms, in stillanother embodiment at least about 20 carbon atoms, in another embodimentat least about 21 carbon atoms, in yet another embodiment at least about22 carbon atoms, in still another embodiment at least about 23 carbonatoms, in another embodiment at least about 24 carbon atoms, in yetanother embodiment at least about 25 carbon atoms, in still anotherembodiment at least about 26 carbon atoms, in another embodiment atleast about 27 carbon atoms, in yet another embodiment at least about 28carbon atoms, in still another embodiment at least about 29 carbonatoms, in another embodiment at least about 30 carbon atoms, in yetanother embodiment at least about 31 carbon atoms, and in still anotherembodiment at least about 32 carbon atoms, and in one embodiment with nomore than about 50 carbon atoms, although the number of carbon atoms canbe outside of these ranges, (iii) an arylalkyl group (includingsubstituted and unsubstituted arylalkyl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in either the aryl or the alkylportion of the arylalkyl group), in one embodiment with at least about 6carbon atoms, in another embodiment with at least about 7 carbon atoms,in another embodiment with at least about 8 carbon atoms, in anotherembodiment at least about 9 carbon atoms, in yet another embodiment atleast about 10 carbon atoms, in still another embodiment at least about11 carbon atoms, in another embodiment at least about 12 carbon atoms,in yet another embodiment at least about 13 carbon atoms, in stillanother embodiment at least about 14 carbon atoms, in another embodimentat least about 15 carbon atoms, in yet another embodiment at least about16 carbon atoms, in still another embodiment at least about 17 carbonatoms, in another embodiment at least about 18 carbon atoms, in yetanother embodiment at least about 19 carbon atoms, in still anotherembodiment at least about 20 carbon atoms, in another embodiment atleast about 21 carbon atoms, in yet another embodiment at least about 22carbon atoms, in still another embodiment at least about 23 carbonatoms, in another embodiment at least about 24 carbon atoms, in yetanother embodiment at least about 25 carbon atoms, in still anotherembodiment at least about 26 carbon atoms, in another embodiment atleast about 27 carbon atoms, in yet another embodiment at least about 28carbon atoms, in still another embodiment at least about 29 carbonatoms, in another embodiment at least about 30 carbon atoms, in yetanother embodiment at least about 31 carbon atoms, and in still anotherembodiment at least about 32 carbon atoms, and in one embodiment with nomore than about 50 carbon atoms, although the number of carbon atoms canbe outside of these ranges, such as benzyl or the like, or (iv) analkylaryl group (including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present ineither the alkyl or the aryl portion of the alkylaryl group), in oneembodiment with at least about 6 carbon atoms, in another embodimentwith at least about 7 carbon atoms, in another embodiment with at leastabout 8 carbon atoms, in another embodiment at least about 9 carbonatoms, in yet another embodiment at least about 10 carbon atoms, instill another embodiment at least about 11 carbon atoms, in anotherembodiment at least about 12 carbon atoms, in yet another embodiment atleast about 13 carbon atoms, in still another embodiment at least about14 carbon atoms, in another embodiment at least about 15 carbon atoms,in yet another embodiment at least about 16 carbon atoms, in stillanother embodiment at least about 17 carbon atoms, in another embodimentat least about 18 carbon atoms, in yet another embodiment at least about19 carbon atoms, in still another embodiment at least about 20 carbonatoms, in another embodiment at least about 21 carbon atoms, in yetanother embodiment at least about 22 carbon atoms, in still anotherembodiment at least about 23 carbon atoms, in another embodiment atleast about 24 carbon atoms, in yet another embodiment at least about 25carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms, and in one embodiment with no more than about 50 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like, R₈ is (i) a hydrogen atom, (ii) an alkyl group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the alkyl group), in one embodimentwith at least about 1 carbon atom, and in one embodiment with no morethan about 50 carbon atoms, in another embodiment with no more thanabout 18 carbon atoms, and in yet another embodiment with no more thanabout 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (iii) an aryl group (including substituted andunsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about5 carbon atoms, and in another embodiment with at least about 6 carbonatoms, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, and in yetanother embodiment with no more than about 12 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in either thearyl or the alkyl portion of the arylalkyl group), in one embodimentwith at least about 6 carbon atoms, and in another embodiment with atleast about 7 carbon atoms, and in one embodiment with no more thanabout 50 carbon atoms, in another embodiment with no more than about 18carbon atoms, and in yet another embodiment with no more than about 12carbon atoms, although the number of carbon atoms can be outside ofthese ranges, such as benzyl or the like, or (v) an alkylaryl group(including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like, X is —O— or —NR₉—, and R₉ is (i) a hydrogen atom,(ii) an alkyl group (including linear, branched, saturated, unsaturated,cyclic, substituted, and unsubstituted alkyl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the alkyl group), in oneembodiment with at least about 1 carbon atom, and in one embodiment withno more than about 50 carbon atoms, in another embodiment with no morethan about 18 carbon atoms, and in yet another embodiment with no morethan about 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (iii) an aryl group (including substituted andunsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about5 carbon atoms, and in another embodiment with at least about 6 carbonatoms, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, and in yetanother embodiment with no more than about 12 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in either thearyl or the alkyl portion of the arylalkyl group), in one embodimentwith at least about 6 carbon atoms, and in another embodiment with atleast about 7 carbon atoms, and in one embodiment with no more thanabout 50 carbon atoms, in another embodiment with no more than about 18carbon atoms, and in yet another embodiment with no more than about 12carbon atoms, although the number of carbon atoms can be outside ofthese ranges, such as benzyl or the like, or (v) an alkylaryl group(including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like.

For the compounds of the formulae

the substituents on the substituted alkyl, alkylene, aryl, arylene,arylalkyl, arylalkylene, alkylaryl, and alkylarylene groups can be (butare not limited to) hydroxy groups, halogen atoms, amine groups, iminegroups, ammonium groups, cyano groups, pyridine groups, pyridiniumgroups, ether groups, aldehyde groups, ketone groups, ester groups,amide groups, carbonyl groups, thiocarbonyl groups, sulfate groups,sulfonate groups, sulfonic acid groups, sulfide groups, sulfoxidegroups, phosphine groups, phosphonium groups, phosphate groups, nitrilegroups, mercapto groups, nitro groups, nitroso groups, sulfone groups,acyl groups, acid anhydride groups, azide groups, azo groups, cyanatogroups, isocyanato groups, thiocyanato groups, isothiocyanato groups,carboxylate groups, carboxylic acid groups, urethane groups, ureagroups, mixtures thereof, and the like, wherein two or more substituentscan be joined together to form a ring.

It should be noted that since hetero atoms can be present in the alkyl,alkylene, aryl, arylene, arylalkyl, arylalkylene, alkylaryl, andalkylarylene groups, these groups also include alkoxy, alkyleneoxy,aryloxy, aryleneoxy, arylalkyloxy, arylalkyleneoxy, alkylaryloxy,alkylaryleneoxy, and the like, including those wherein an oxygen atomthereof is the point of attachment of the R group, and including (butnot limited to) those of the formulae—(C_(a)H_(2a)O)bR₁₀and—(OC_(a)H_(2a))bOR₁₀wherein a is an integer representing the number of carbon atoms in thealkyleneoxy, aryleneoxy, arylalkyleneoxy, or alkylaryleneoxy group,being in various embodiments 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32,33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, or50, although the value of a can be outside of these ranges, b is aninteger representing the number of repeat alkyleneoxy, aryleneoxy,arylalkyleneoxy, or alkylaryleneoxy units, being in one embodiment atleast 1, in another embodiment at least about 2, in yet anotherembodiment at least about 5, and in still another embodiment at leastabout 10, and being in one embodiment no more than about 200, in anotherembodiment no more than about 150, in yet another embodiment no morethan about 100, and in still another embodiment no more than about 50,although the value of b can be outside of these ranges, and R₁₀ is (i) ahydrogen atom, (ii) an alkyl group (including linear, branched,saturated, unsaturated, cyclic, unsubstituted, and substituted alkylgroups, and wherein hetero atoms, such as oxygen, nitrogen, sulfur,silicon, phosphorus, and the like either may or may not be present inthe alkyl group), in one embodiment with at least about 1 carbon atom,in another embodiment with at least about 2 carbon atoms, in anotherembodiment with at least about 4 carbon atoms, in yet another embodimentwith at least about 6 carbon atoms, in still another embodiment with atleast about 8 carbon atoms, in another embodiment with at least about 10carbon atoms, in yet another embodiment with at least about 12 carbonatoms, in still another embodiment with at least about 14 carbon atoms,in another embodiment with at least about 16 carbon atoms, in yetanother embodiment with at least about 18 carbon atoms, in still anotherembodiment with at least about 20 carbon atoms, in another embodimentwith at least about 22 carbon atoms, in yet another embodiment with atleast about 24 carbon atoms, in still another embodiment with at leastabout 26 carbon atoms, in another embodiment with at least about 28carbon atoms, in yet another embodiment with at least about 30 carbonatoms, in still another embodiment with at least about 32 carbon atoms,in another embodiment with at least about 34 carbon atoms, in yetanother embodiment with at least about 36 carbon atoms, in still anotherembodiment with at least about 38 carbon atoms, in another embodimentwith at least about 40 carbon atoms, in yet another embodiment with atleast about 42 carbon atoms, in still another embodiment with at leastabout 44 carbon atoms, in another embodiment with at least about 46carbon atoms, in yet another embodiment with at least about 48 carbonatoms, and in still another embodiment with at least about 50 carbonatoms, and in one embodiment with no more than about 100 carbon atoms,in another embodiment with no more than about 70 carbon atoms, in yetanother embodiment with no more than about 60 carbon atoms, and in stillanother embodiment with no more than about 50 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iii) an arylgroup (including unsubstituted and substituted aryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in the aryl group), in oneembodiment with at least about 6 carbon atoms, in another embodimentwith at least about 10 carbon atoms, in yet another embodiment with atleast about 13 carbon atoms, in still another embodiment with at leastabout 14 carbon atoms, in another embodiment with at least about 16carbon atoms, in yet another embodiment with at least about 18 carbonatoms, in still another embodiment with at least about 20 carbon atoms,in another embodiment with at least about 22 carbon atoms, in yetanother embodiment with at least about 24 carbon atoms, in still anotherembodiment with at least about 26 carbon atoms, in another embodimentwith at least about 28 carbon atoms, in yet another embodiment with atleast about 30 carbon atoms, in still another embodiment with at leastabout 32 carbon atoms, in another embodiment with at least about 34carbon atoms, in yet another embodiment with at least about 36 carbonatoms, in still another embodiment with at least about 38 carbon atoms,in another embodiment with at least about 40 carbon atoms, in yetanother embodiment with at least about 42 carbon atoms, in still anotherembodiment with at least about 44 carbon atoms, in another embodimentwith at least about 46 carbon atoms, in yet another embodiment with atleast about 48 carbon atoms, and in still another embodiment with atleast about 50 carbon atoms, and in one embodiment with no more thanabout 100 carbon atoms, in another embodiment with no more than about 75carbon atoms, in yet another embodiment with no more than about 60carbon atoms, and in still another embodiment with no more than about 50carbon atoms, although the number of carbon atoms can be outside ofthese ranges, (iv) an arylalkyl group (including unsubstituted andsubstituted arylalkyl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in either or both of the alkyl portion and the arylportion of the arylalkyl group), in one embodiment with at least about 6carbon atoms, in another embodiment with at least about 7 carbon atoms,in yet another embodiment with at least about 8 carbon atoms, in anotherembodiment with at least about 10 carbon atoms, in yet anotherembodiment with at least about 12 carbon atoms, in still anotherembodiment with at least about 14 carbon atoms, in another embodimentwith at least about 16 carbon atoms, in yet another embodiment with atleast about 18 carbon atoms, in still another embodiment with at leastabout 20 carbon atoms, in another embodiment with at least about 22carbon atoms, in yet another embodiment with at least about 24 carbonatoms, in still another embodiment with at least about 26 carbon atoms,in another embodiment with at least about 28 carbon atoms, in yetanother embodiment with at least about 30 carbon atoms, in still anotherembodiment with at least about 32 carbon atoms, in another embodimentwith at least about 34 carbon atoms, in yet another embodiment with atleast about 36 carbon atoms, in another embodiment with at least about38 carbon atoms, in yet another embodiment with at least about 40 carbonatoms, in still another embodiment with at least about 42 carbon atoms,in another embodiment with at least about 44 carbon atoms, in yetanother embodiment with at least about 46 carbon atoms, in still anotherembodiment with at least about 48 carbon atoms, and in anotherembodiment with at least about 50 carbon atoms, and in one embodimentwith no more than about 200 carbon atoms, in another embodiment with nomore than about 100 carbon atoms, in yet another embodiment with no morethan about 60 carbon atoms, and in still another embodiment with no morethan about 50 carbon atoms, although the number of carbon atoms can beoutside of these ranges, or (v) an alkylaryl group (includingunsubstituted and substituted alkylaryl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in either or both of the alkylportion and the aryl portion of the alkylaryl group), in one embodimentwith at least about 6 carbon atoms, in another embodiment with at leastabout 7 carbon atoms, in yet another embodiment with at least about 8carbon atoms, in another embodiment with at least about 10 carbon atoms,in yet another embodiment with at least about 12 carbon atoms, in stillanother embodiment with at least about 14 carbon atoms, in anotherembodiment with at least about 16 carbon atoms, in yet anotherembodiment with at least about 18 carbon atoms, in still anotherembodiment with at least about 20 carbon atoms, in another embodimentwith at least about 22 carbon atoms, in yet another embodiment with atleast about 24 carbon atoms, in still another embodiment with at leastabout 26 carbon atoms, in another embodiment with at least about 28carbon atoms, in yet another embodiment with at least about 30 carbonatoms, in still another embodiment with at least about 32 carbon atoms,in another embodiment with at least about 34 carbon atoms, in yetanother embodiment with at least about 36 carbon atoms, in anotherembodiment with at least about 38 carbon atoms, in yet anotherembodiment with at least about 40 carbon atoms, in still anotherembodiment with at least about 42 carbon atoms, in another embodimentwith at least about 44 carbon atoms, in yet another embodiment with atleast about 46 carbon atoms, in still another embodiment with at leastabout 48 carbon atoms, and in another embodiment with at least about 50carbon atoms, and in one embodiment with no more than about 200 carbonatoms, in another embodiment with no more than about 100 carbon atoms,in yet another embodiment with no more than about 60 carbon atoms, andin still another embodiment with no more than about 50 carbon atoms,although the number of carbon atoms can be outside of these ranges.

Further, since hetero atoms can be present in these groups, these groupsalso include heterocyclic groups.

In one specific embodiment, the total number of carbon atoms inR₁+R₂+R₃+R₄+R₅+(R₆ or R₆₆)+R₇+R₈+R₉ is no more than about 200, inanother embodiment no more than about 100, and in yet another embodimentno more than about 70, although the total number of carbon atoms can beoutside of these ranges.

In one specific embodiment, the total number of carbon atoms inR₁+R₂+R₃+R₄+R₅+(R₆ or R₆₆)+R₇+R₈+R₉ is at least about 12, in anotherembodiment at least about 13, in yet another embodiment at least about14, in still another embodiment at least about 15, in another embodimentat least about 16, in yet another embodiment at least about 17, in stillanother embodiment at least about 18, in another embodiment at leastabout 19, in yet another embodiment at least about 20, in yet anotherembodiment at least about 21, in another embodiment at least about 22,in yet another embodiment at least about 23, in yet another embodimentat least about 24, in another embodiment at least about 25, in yetanother embodiment at least about 26, in yet another embodiment at leastabout 27, in another embodiment at least about 28, in yet anotherembodiment at least about 29, in yet another embodiment at least about30, in another embodiment at least about 31, in yet another embodimentat least about 32, in yet another embodiment at least about 33, inanother embodiment at least about 34, in yet another embodiment at leastabout 35, in yet another embodiment at least about 36, in anotherembodiment at least about 37, in yet another embodiment at least about38, in yet another embodiment at least about 39, in another embodimentat least about 40, in yet another embodiment at least about 41, in yetanother embodiment at least about 42, in another embodiment at leastabout 43, in yet another embodiment at least about 44, in yet anotherembodiment at least about 45, in another embodiment at least about 46,in yet another embodiment at least about 47, and in yet anotherembodiment at least about 48, although the total number of carbon atomscan be outside of these ranges.

In one specific embodiment, G is (I) an alkyl group having in oneembodiment at least about 8 carbon atoms, in another embodiment at leastabout 9 carbon atoms, in yet another embodiment at least about 10 carbonatoms, in still another embodiment at least about 11 carbon atoms, inanother embodiment at least about 12 carbon atoms, in yet anotherembodiment at least about 13 carbon atoms, in still another embodimentat least about 14 carbon atoms, in another embodiment at least about 15carbon atoms, in yet another embodiment at least about 16 carbon atoms,in still another embodiment at least about 17 carbon atoms, in anotherembodiment at least about 18 carbon atoms, in yet another embodiment atleast about 19 carbon atoms, in still another embodiment at least about20 carbon atoms, in another embodiment at least about 21 carbon atoms,in yet another embodiment at least about 22 carbon atoms, in stillanother embodiment at least about 23 carbon atoms, in another embodimentat least about 24 carbon atoms, in yet another embodiment at least about25 carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms, (II) an arylalkyl group having at least about 14 carbon atoms,wherein the alkyl portion thereof has in one embodiment at least about 8carbon atoms, in another embodiment at least about 9 carbon atoms, inyet another embodiment at least about 10 carbon atoms, in still anotherembodiment at least about 11 carbon atoms, in another embodiment atleast about 12 carbon atoms, in yet another embodiment at least about 13carbon atoms, in still another embodiment at least about 14 carbonatoms, in another embodiment at least about 15 carbon atoms, in yetanother embodiment at least about 16 carbon atoms, in still anotherembodiment at least about 17 carbon atoms, in another embodiment atleast about 18 carbon atoms, in yet another embodiment at least about 19carbon atoms, in still another embodiment at least about 20 carbonatoms, in another embodiment at least about 21 carbon atoms, in yetanother embodiment at least about 22 carbon atoms, in still anotherembodiment at least about 23 carbon atoms, in another embodiment atleast about 24 carbon atoms, in yet another embodiment at least about 25carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms, (III) an alkylaryl group having at least about 14 carbon atoms,wherein the alkyl portion thereof has in one embodiment at least about 8carbon atoms, in another embodiment at least about 9 carbon atoms, inyet another embodiment at least about 10 carbon atoms, in still anotherembodiment at least about 11 carbon atoms, in another embodiment atleast about 12 carbon atoms, in yet another embodiment at least about 13carbon atoms, in still another embodiment at least about 14 carbonatoms, in another embodiment at least about 15 carbon atoms, in yetanother embodiment at least about 16 carbon atoms, in still anotherembodiment at least about 17 carbon atoms, in another embodiment atleast about 18 carbon atoms, in yet another embodiment at least about 19carbon atoms, in still another embodiment at least about 20 carbonatoms, in another embodiment at least about 21 carbon atoms, in yetanother embodiment at least about 22 carbon atoms, in still anotherembodiment at least about 23 carbon atoms, in another embodiment atleast about 24 carbon atoms, in yet another embodiment at least about 25carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms, or (IV) a group of one of the formulae

wherein R₇ is (i) an alkyl group having in one embodiment at least about8 carbon atoms, in another embodiment at least about 9 carbon atoms, inyet another embodiment at least about 10 carbon atoms, in still anotherembodiment at least about 11 carbon atoms, in another embodiment atleast about 12 carbon atoms, in yet another embodiment at least about 13carbon atoms, in still another embodiment at least about 14 carbonatoms, in another embodiment at least about 15 carbon atoms, in yetanother embodiment at least about 16 carbon atoms, in still anotherembodiment at least about 17 carbon atoms, in another embodiment atleast about 18 carbon atoms, in yet another embodiment at least about 19carbon atoms, in still another embodiment at least about 20 carbonatoms, in another embodiment at least about 21 carbon atoms, in yetanother embodiment at least about 22 carbon atoms, in still anotherembodiment at least about 23 carbon atoms, in another embodiment atleast about 24 carbon atoms, in yet another embodiment at least about 25carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms, (ii) an arylalkyl group having at least about 14 carbon atoms,wherein the alkyl portion thereof has in one embodiment at least about 8carbon atoms, in another embodiment at least about 9 carbon atoms, inyet another embodiment at least about 10 carbon atoms, in still anotherembodiment at least about 11 carbon atoms, in another embodiment atleast about 12 carbon atoms, in yet another embodiment at least about 13carbon atoms, in still another embodiment at least about 14 carbonatoms, in another embodiment at least about 15 carbon atoms, in yetanother embodiment at least about 16 carbon atoms, in still anotherembodiment at least about 17 carbon atoms, in another embodiment atleast about 18 carbon atoms, in yet another embodiment at least about 19carbon atoms, in still another embodiment at least about 20 carbonatoms, in another embodiment at least about 21 carbon atoms, in yetanother embodiment at least about 22 carbon atoms, in still anotherembodiment at least about 23 carbon atoms, in another embodiment atleast about 24 carbon atoms, in yet another embodiment at least about 25carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms, or (iii) an alkylaryl group having at least about 14 carbonatoms, wherein the alkyl portion thereof has in one embodiment at leastabout 8 carbon atoms, in another embodiment at least about 9 carbonatoms, in yet another embodiment at least about 10 carbon atoms, instill another embodiment at least about 11 carbon atoms, in anotherembodiment at least about 12 carbon atoms, in yet another embodiment atleast about 13 carbon atoms, in still another embodiment at least about14 carbon atoms, in another embodiment at least about 15 carbon atoms,in yet another embodiment at least about 16 carbon atoms, in stillanother embodiment at least about 17 carbon atoms, in another embodimentat least about 18 carbon atoms, in yet another embodiment at least about19 carbon atoms, in still another embodiment at least about 20 carbonatoms, in another embodiment at least about 21 carbon atoms, in yetanother embodiment at least about 22 carbon atoms, in still anotherembodiment at least about 23 carbon atoms, in another embodiment atleast about 24 carbon atoms, in yet another embodiment at least about 25carbon atoms, in still another embodiment at least about 26 carbonatoms, in another embodiment at least about 27 carbon atoms, in yetanother embodiment at least about 28 carbon atoms, in still anotherembodiment at least about 29 carbon atoms, in another embodiment atleast about 30 carbon atoms, in yet another embodiment at least about 31carbon atoms, and in still another embodiment at least about 32 carbonatoms.

The above formula encompasses monomeric materials. In addition, theabove formula encompasses dimeric materials containing two moieties ofthe formula

wherein each G, independently of the other, is (1) an alkylene group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkylene groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the alkylene group), in oneembodiment with at least about 1 carbon atom, and in one embodiment withno more than about 50 carbon atoms, in another embodiment with no morethan about 18 carbon atoms, and in yet another embodiment with no morethan about 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (2) an arylene group (including unsubstitutedand substituted arylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in the arylene group), in one embodiment with atleast about 5 carbon atoms, and in another embodiment with at leastabout 6 carbon atoms, and in one embodiment with no more than about 50carbon atoms, in another embodiment with no more than about 18 carbonatoms, in yet another embodiment with no more than about 12 carbonatoms, although the number of carbon atoms can be outside of theseranges, (3) an arylalkylene group (including unsubstituted andsubstituted arylalkylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the aryl and the alkylportions of the arylalkylene group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms, inyet another embodiment with no more than about 12 carbon atoms, althoughthe number of carbon atoms can be outside of these ranges, such asbenzylene or the like, including (a) arylalkylene groups wherein boththe aryl and the alkyl portions form the linkage between the two

moieties, such as

and the like, and (b) arylalkylene groups wherein only the alkyl portionforms the linkage between the two

moieties, such as

and the like, (4) an alkylarylene group (including unsubstituted andsubstituted alkylarylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either or both of the aryl and the alkylportions of the alkylarylene group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms, inyet another embodiment with no more than about 12 carbon atoms, althoughthe number of carbon atoms can be outside of these ranges, such astolylene, phenylethylene, or the like, including (a) alkylarylene groupswherein both the aryl and the alkyl portions form the linkage betweenthe two

moieties, such as

and the like, and (b) alkylarylene groups wherein only the aryl portionforms the linkage between the two

moieties, such as

and the like, (5) a group of the formula

(6) a group of the formula

(7) a group of the formula

or (8) a group of the formula

wherein each R₇, independently of the other, is (i) an alkylene group(including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkylene groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the alkylene group), in oneembodiment with at least about 1 carbon atom, and in one embodiment withno more than about 50 carbon atoms, in another embodiment with no morethan about 18 carbon atoms, and in yet another embodiment with no morethan about 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (ii) an arylene group (including substitutedand unsubstituted arylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in the arylene group), in one embodiment with atleast about 5 carbon atoms, and in another embodiment with at leastabout 6 carbon atoms, and in one embodiment with no more than about 50carbon atoms, in another embodiment with no more than about 18 carbonatoms, and in yet another embodiment with no more than about 12 carbonatoms, although the number of carbon atoms can be outside of theseranges, (iii) an arylalkylene group (including substituted andunsubstituted arylalkylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the aryl or the alkyl portion of thearylalkylene group), in one embodiment with at least about 6 carbonatoms, and in another embodiment with at least about 7 carbon atoms, andin one embodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as benzylene or thelike, or (iv) an alkylarylene group (including substituted andunsubstituted alkylarylene groups, and wherein hetero atoms, such asoxygen, nitrogen, sulfur, silicon, phosphorus, and the like either mayor may not be present in either the alkyl or the aryl portion of thealkylarylene group), in one embodiment with at least about 6 carbonatoms, and in another embodiment with at least about 7 carbon atoms, andin one embodiment with no more than about 50 carbon atoms, in anotherembodiment with no more than about 18 carbon atoms, and in yet anotherembodiment with no more than about 12 carbon atoms, although the numberof carbon atoms can be outside of these ranges, such as tolylene or thelike, each R₈, independently of the other, is (i) a hydrogen atom, (ii)an alkyl group (including linear, branched, saturated, unsaturated,cyclic, substituted, and unsubstituted alkyl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the alkyl group), in oneembodiment with at least about 1 carbon atom, and in one embodiment withno more than about 50 carbon atoms, in another embodiment with no morethan about 18 carbon atoms, and in yet another embodiment with no morethan about 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (iii) an aryl group (including substituted andunsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about5 carbon atoms, and in another embodiment with at least about 6 carbonatoms, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, and in yetanother embodiment with no more than about 12 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in either thearyl or the alkyl portion of the arylalkyl group), in one embodimentwith at least about 6 carbon atoms, and in another embodiment with atleast about 7 carbon atoms, and in one embodiment with no more thanabout 50 carbon atoms, in another embodiment with no more than about 18carbon atoms, and in yet another embodiment with no more than about 12carbon atoms, although the number of carbon atoms can be outside ofthese ranges, such as benzyl or the like, or (v) an alkylaryl group(including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like, each X, independently of the other, is —O— or—NR₉—, and each R₉, independently of the other, is (i) a hydrogen atom,(ii) an alkyl group (including linear, branched, saturated, unsaturated,cyclic, substituted, and unsubstituted alkyl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in the alkyl group), in oneembodiment with at least about 1 carbon atom, and in one embodiment withno more than about 50 carbon atoms, in another embodiment with no morethan about 18 carbon atoms, and in yet another embodiment with no morethan about 12 carbon atoms, although the number of carbon atoms can beoutside of these ranges, (iii) an aryl group (including substituted andunsubstituted aryl groups, and wherein hetero atoms, such as oxygen,nitrogen, sulfur, silicon, phosphorus, and the like either may or maynot be present in the aryl group), in one embodiment with at least about5 carbon atoms, and in another embodiment with at least about 6 carbonatoms, and in one embodiment with no more than about 50 carbon atoms, inanother embodiment with no more than about 18 carbon atoms, and in yetanother embodiment with no more than about 12 carbon atoms, although thenumber of carbon atoms can be outside of these ranges, (iv) an arylalkylgroup (including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms, such as oxygen, nitrogen, sulfur, silicon,phosphorus, and the like either may or may not be present in either thearyl or the alkyl portion of the arylalkyl group), in one embodimentwith at least about 6 carbon atoms, and in another embodiment with atleast about 7 carbon atoms, and in one embodiment with no more thanabout 50 carbon atoms, in another embodiment with no more than about 18carbon atoms, and in yet another embodiment with no more than about 12carbon atoms, although the number of carbon atoms can be outside ofthese ranges, such as benzyl or the like, or (v) an alkylaryl group(including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, andthe like either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group), in one embodiment with at leastabout 6 carbon atoms, and in another embodiment with at least about 7carbon atoms, and in one embodiment with no more than about 50 carbonatoms, in another embodiment with no more than about 18 carbon atoms,and in yet another embodiment with no more than about 12 carbon atoms,although the number of carbon atoms can be outside of these ranges, suchas tolyl or the like, and wherein the substituents on the substitutedalkyl, alkylene, aryl, arylene, arylalkyl, arylalkylene, alkylaryl, andalkylarylene groups can be (but are not limited to) hydroxy groups,halogen atoms, amine groups, imine groups, ammonium groups, cyanogroups, pyridine groups, pyridinium groups, ether groups, aldehydegroups, ketone groups, ester groups, amide groups, carbonyl groups,thiocarbonyl groups, sulfate groups, sulfonate groups, sulfonic acidgroups, sulfide groups, sulfoxide groups, phosphine groups, phosphoniumgroups, phosphate groups, nitrile groups, mercapto groups, nitro groups,nitroso groups, sulfone groups, acyl groups, acid anhydride groups,azide groups, azo groups, cyanato groups, isocyanato groups, thiocyanatogroups, isothiocyanato groups, carboxylate groups, carboxylic acidgroups, urethane groups, urea groups, mixtures thereof, and the like,wherein two or more substituents can be joined together to form a ring.

It should be noted that since hetero atoms can be present in the alkyl,alkylene, aryl, arylene, arylalkyl, arylalkylene, alkylaryl, andalkylarylene groups, these groups also include alkoxy, alkyleneoxy,aryloxy, aryleneoxy, arylalkyloxy, arylalkyleneoxy, alkylaryloxy,alkylaryleneoxy, and the like, including those wherein an oxygen atomthereof is the point of attachment of the R group, and including (butnot limited to) those of the formulae—(C_(a)H_(2a)O)b-wherein a is an integer representing the number of carbon atoms in thealkyleneoxy, aryleneoxy, arylalkyleneoxy, or alkylaryleneoxy group,being in various embodiments 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32,33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, or50, although the value of a can be outside of these ranges, b is aninteger representing the number of repeat alkyleneoxy, aryleneoxy,arylalkyleneoxy, or alkylaryleneoxy groups, being in one embodiment atleast 1, in another embodiment at least about 2, in yet anotherembodiment at least about 5, and in still another embodiment at leastabout 10, and being in one embodiment no more than about 200, in anotherembodiment no more than about 150, in yet another embodiment no morethan about 100, and in still another embodiment no more than about 50,although the value of b can be outside of these ranges.

Further, since hetero atoms can be present in these groups, these groupsalso include heterocyclic groups.

Examples of such dimeric materials include (but are not limited to)those of the formulae

wherein R represents an alkyl, aryl, arylalkyl, or alkylaryl group asdefined hereinabove having no substituents thereon and no hetero atomstherein,

wherein R represents an alkyl, aryl, arylalkyl, or alkylaryl group asdefined hereinabove having no substituents thereon and no hetero atomstherein, and the like.

Similarly, the above formula encompasses trimeric, tetrameric, andhigher moieties as well as oligomeric materials and polymeric materials,said materials containing three or more moieties of the formula

wherein each R₁, R₂, R₃, R₄, R₅, R₆, R₆₆, G, m, n, and p, independentlyof the others, has the definitions for R₁, R₂, R₃, R₄, R₅, R₆, R₆₆, G,m, n, and p set forth hereinabove and can be either the same as ordifferent from one another, said moieties being linked by a central atomor group of atoms or bonded to a polymeric chain. These materials can bemade by processes analogous to those illustrated herein for themonomeric and dimeric compounds.

The compounds disclosed herein can be any of a wide variety of colors.In one specific embodiment, the compound is of a red color. In anotherspecific embodiment, the compound is of a magenta color.

The colorant compounds disclosed herein can be prepared by any desiredor effective method. Starting materials such as4-bromo-1:9-N-methylanthrapyridone, can be prepared as disclosed in, forexample, “British Intelligence Objectives Subcommittee Report 1484”,Publication Board No. 86139, Library of Congress, Washington, D.C.,1947, p. 46-47, the disclosure of which is totally incorporated byreference. This material is also commercially available from, forexample, Hangsu Aolunda High Tech Industry Co. Ltd., Shanghai, China.Further background on syntheses of starting materials and relatedcompounds is disclosed in, for example, U.S. Pat. Nos. 6,152,969,5,340,910, 4,386,206, 4,745,174, and 2,644,821, the disclosures of eachof which are totally incorporated herein by reference.

Compounds of the formula

and compounds of the formula

can be prepared by analogous processes. Hereinafter, exemplary syntheticmethods will be provided for compounds of the formula

it is to be understood that these methods can also be used to preparecompounds of the formula

by employing analogous starting materials.

Compounds of the formula

can be prepared from brominated compounds of the formula

by reacting the brominated starting material with the correspondingaminobenzene having the desired alcohol group of the formula —R₆OH inthe presence of a base and heating, as follows:

The brominated starting material and the aminobenzene are present in anydesired or effective relative amounts, in one embodiment at least about1 mole of aminobenzene per every one mole of brominated startingmaterial, in another embodiment at least about 5 moles of aminobenzeneper every one mole of brominated starting material, and in yet anotherembodiment at least about 12 moles of aminobenzene per every one mole ofbrominated starting material, and in one embodiment no more than about20 moles of aminobenzene per every one mole of brominated startingmaterial, in another embodiment no more than about 15 moles ofaminobenzene per every one mole of brominated starting material, and inyet another embodiment no more than about 13 moles of aminobenzene perevery one mole of brominated starting material, although the relativeamounts of aminobenzene and brominated starting material can be outsideof these ranges.

Any desired or effective base can be employed. Examples of suitablebases include (but are not limited to) sodium carbonate, potassiumcarbonate, calcium carbonate, calcium oxide, zinc oxide, and the like,as well as mixtures thereof. The base is present in any desired oreffective amount, in one embodiment at least about 0.5 mole of base perevery one mole of brominated starting material, in another embodiment atleast about 1 mole of base per every one mole of brominated startingmaterial, and in yet another embodiment at least about 2 moles of baseper every one mole of brominated starting material, and in oneembodiment no more than about 5 moles of base per every one mole ofbrominated starting material, in another embodiment no more than about 4moles of base per every one mole of brominated starting material, and inyet another embodiment no more than about 3 moles of base per every onemole of brominated starting material, although the relative amounts ofaniline and brominated starting material can be outside of these ranges.

Optionally, if desired, a catalyst for the reaction can be employed,such as a copper salt, including (but not limited to) cupric acetate,copper sulfate, copper II acetate monohydrate, copper powder, and thelike, in any desired or effective amount.

While not required, if desired, an optional solvent can be employed. Ifused, any desired or effective solvent can be used, including polaraprotic solvents such as N-methylpyrrolidinone, dimethyl formamide,dimethyl sulfoxide, sulfolane, or the like, as well as mixtures thereof,in any desired or effective amount, in one embodiment in a ratio byweight of at least about 1 part by weight brominated starting materialper every hundred parts by weight solvent, and in one embodiment in aratio by weight of no more than about 20 parts by weight brominatedstarting material per every hundred parts by weight solvent, althoughthe relative amounts of solvent and brominated starting material can beoutside of these ranges.

The reaction mixture containing the aminobenzene and the brominatedstarting material is heated to any desirable or effective temperature toeffect the reaction, in one embodiment at least about 100° C., inanother embodiment at least about 120° C., and in yet another embodimentat least about 180° C., and in one embodiment no more than about 250°C., in another embodiment no more than about 200° C., and in yet anotherembodiment no more than about 190° C., although the temperature can beoutside of these ranges.

The reaction between the aminobenzene and the brominated startingmaterial is allowed to proceed for any desired or effective period oftime, in one embodiment at least about 10 minutes, in another embodimentat least about 1 hour, and in yet another embodiment at least about 1.5hour, and in one embodiment no more than about 4 days, in anotherembodiment no more than about 1 day, and in yet another embodiment nomore than about 2 hours, although the reaction time can be outside ofthese ranges.

Upon completion of the reaction, the compound of the formula

can be recovered by quenching the reaction mixture with a mixture ofacid and water, followed by filtration, washing, and drying. Any desiredor effective acid can be employed, such as hydrochloric acid, sulfuricacid, phosphoric acid, or the like, as well as mixtures thereof, in anydesired or effective concentration, in one specific embodiment at leastabout 1 percent by weight acid in water, and in one specific embodimentno more than about 20 percent by weight acid in water, although theconcentration can be outside of these ranges.

The alcohol-substituted compound of the formula

can be converted to an ester-substituted compound of the formula

by preparing a reaction mixture by admixing (1) the alcohol-substitutedcompound (2) a solvent, and (3) an esterification compound such as ananhydride of the formula

in which reaction mixture upon heating is formed an ester-substitutedcompound as follows

The alcohol-substituted compound and the anhydride are present in anydesired or effective relative amounts, in one embodiment at least about1 mole of anhydride per every one mole of alcohol-substituted compound,and in one embodiment no more than about 1.1 moles of anhydride perevery one mole of alcohol-substituted compound, although the amount ofanhydride can be outside of these ranges.

Examples of suitable solvents include acetic acid, propionic acid,formic acid, butyric acid, dimethyl formamide, dimethyl sulfoxide,hexamethyl phosphorus triamide (HMPA), tetrahydrofuran, or the like, aswell as mixtures thereof. The solvent is present in any desired oreffective amount, in one embodiment at least about 25 grams ofalcohol-substituted compound per every one liter of solvent, and inanother embodiment at least about 100 grams of alcohol-substitutedcompound per every one liter of solvent, and in one embodiment no morethan about 200 grams of alcohol-substituted compound per every one literof solvent, although the amount of solvent can be outside of theseranges.

The reaction mixture containing the alcohol-substituted compound, thesolvent, and the anhydride is heated to any desirable or effectivetemperature, in one embodiment at least about 25° C., and in anotherembodiment at least about 40° C., and in one embodiment no more thanabout 100° C., and in another embodiment no more than about 60° C.,although the temperature can be outside of these ranges.

The reaction mixture containing the alcohol-substituted compound, thesolvent, and the anhydride is heated for any desirable or effectiveperiod of time, in one embodiment at least about 2.5 hours, and inanother embodiment at least about 3 hours, and in one embodiment no morethan about 5 hours, although the heating time can be outside of theseranges. Reaction completion can be determined by thin layerchromatography of the reaction mixture to detect the presence ofunreacted reactants.

The alcohol-substituted compound of the formula

can also be converted to an ester-substituted compound of the formula

by admixing (1) the alcohol-substituted compound, (2) an esterificationcompound such as a carboxylic acid of the formula R₇COOH, (3) a solvent,and (4) an optional esterification catalyst, and heating the reactionmixture, as follows:

The alcohol-substituted compound and the carboxylic acid are present inany desired or effective relative amounts, in one embodiment at leastabout 0.9 mole of carboxylic acid per every one mole ofalcohol-substituted compound, in another embodiment at least about 0.95mole of carboxylic acid per mole of alcohol-substituted compound, and inyet another embodiment at least about 1 mole of carboxylic acid per moleof alcohol-substituted compound, and in one embodiment no more thanabout 2 moles of carboxylic acid per mole of alcohol-substitutedcompound, in another embodiment no more than about 1.05 moles ofcarboxylic acid per mole of alcohol-substituted compound, and in yetanother embodiment no more than about 1 mole of carboxylic acid per moleof alcohol-substituted compound, although the relative amounts ofcarboxylic acid and alcohol-substituted compound can be outside of theseranges.

When the optional esterification catalyst is present, any desired oreffective esterification catalyst can be used, such as para-toluenesulfonic acid, dibutyl tin dilaurate, or the like, as well as mixturesthereof. The esterification catalyst is present in any desired oreffective amount, in one embodiment at least about 0.05 mole ofesterification catalyst per every one mole of alcohol-substitutedcompound, and in one embodiment no more than about 0.5 mole ofesterification catalyst per mole of alcohol-substituted compound,although the amount of esterification catalyst can be outside of theseranges.

Any desired or effective solvent can be used. Examples of suitablesolvents include xylene, toluene, benzene, chlorobenzene, nitrobenzene,dichlorobenzene, and the like, as well as mixtures thereof. Thereactants are present in the solvent in any desired or effective amount,in one embodiment at least about 25 grams of alcohol-substitutedcompound per every one liter of solvent, in another embodiment at leastabout 50 grams of alcohol-substituted compound per every one liter ofsolvent, and in yet another embodiment at least about 100 grams ofalcohol-substituted compound per every one liter of solvent, and in oneembodiment no more than about 200 grams of alcohol-substituted compoundper every one liter of solvent, in another embodiment no more than about150 grams of alcohol-substituted compound per every one liter ofsolvent, and in yet another embodiment no more than about 100 grams ofalcohol-substituted compound per every one liter of solvent, althoughthe amount of solvent can be outside of these ranges.

The reaction mixture containing the alcohol-substituted compound, thecarboxylic acid, the solvent, and the optional esterification catalystis heated to any desirable or effective temperature, typically thereflux temperature of the selected solvent, in one embodiment at leastabout 100° C., and in one embodiment no more than about 130° C.,although the temperature can be outside of these ranges.

The reaction mixture containing the alcohol-substituted compound, thecarboxylic acid, the solvent, and the optional esterification catalystis heated for any desirable or effective period of time, in oneembodiment at least about 2 hours, in another embodiment at least about24 hours, and in one embodiment no more than about 72 hours, and inanother embodiment no more than about 48 hours, although the heatingtime can be outside of these ranges.

The compound of the formula

can be recovered from the reaction mixture as a solid by filtration,followed by washing and drying. If desired, purification can be carriedout by filtration, redissolution in the solvent, heating, cooling,precipitating the compound from the solution, filtering, washing thecompound with a solvent such as methanol, ethanol, or the like, andrepeating this cycle until thin layer chromatography of the collectedsolid indicates that there is no detectable unreacted reactant presentin the solid.

The alcohol-substituted compound of the formula

can be converted to a urethane-substituted compound of the formula

by reacting the alcohol-substituted compound with an isocyanate, asfollows:

Isocyanates react with alcohols to form urethanes. For example, amonoisocyanate reacts with an alcohol to form a urethane as follows:

wherein R_(a) and R_(b) each, independently of the other, is an alkylgroup (including linear, branched, saturated, unsaturated, cyclic,unsubstituted, and substituted alkyl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the alkyl group), typically withfrom about 5 to about 100 carbon atoms, although the number of carbonatoms can be outside of this range, an aryl group (includingunsubstituted and substituted aryl groups, and wherein hetero atoms,such as oxygen, nitrogen, sulfur, silicon, phosphorus, and the likeeither may or may not be present in the aryl group), typically with fromabout 5 to about 20 carbon atoms, although the number of carbon atomscan be outside of this range, an arylalkyl group (includingunsubstituted and substituted arylalkyl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in either or both of the alkylportion and the aryl portion of the arylalkyl group), typically withfrom about 6 to about 50 carbon atoms, although the number of carbonatoms can be outside of this range, or an alkylaryl group (includingunsubstituted and substituted alkylaryl groups, and wherein heteroatoms, such as oxygen, nitrogen, sulfur, silicon, phosphorus, and thelike either may or may not be present in either or both of the alkylportion and the aryl portion of the alkylaryl group), typically withfrom about 6 to about 50 carbon atoms, although the number of carbonatoms can be outside of this range, and wherein the substituents on thesubstituted alkyl, alkylene, aryl, arylene, arylalkyl, arylalkylene,alkylaryl, and alkylarylene groups can be (but are not limited to)hydroxy groups, halogen atoms, amine groups, imine groups, ammoniumgroups, cyano groups, pyridine groups, pyridinium groups, ether groups,aldehyde groups, ketone groups, ester groups, amide groups, carbonylgroups, thiocarbonyl groups, sulfate groups, sulfonate groups, sulfidegroups, sulfoxide groups, phosphine groups, phosphonium groups,phosphate groups, nitrile groups, mercapto groups, nitro groups, nitrosogroups, sulfone groups, acyl groups, acid anhydride groups, azidegroups, azo groups, cyanato groups, isocyanato groups, thiocyanatogroups, isothiocyanato groups, mixtures thereof, and the like, whereintwo or more substituents can be joined together to form a ring.Diisocyanates react similarly; for example, isophorone diisocyanatereacts with two moles of alcohol to form a diurethane as follows:

Examples of suitable isocyanates include monoisocyanates, diisocyanates,triisocyanates, copolymers of a diisocyanate, copolymers of atriisocyanate, polyisocyanates (having more than three isocyanatefunctional groups), and the like, as well as mixtures thereof. Examplesof monoisocyanates include octadecylisocyanate; hexadecylisocyanate;octylisocyanate; butyl and t-butylisocyanate; cyclohexyl isocyanate;adamantyl isocyanate; ethylisocyanatoacetate; ethoxycarbonylisocyanate;phenylisocyanate; alphamethylbenzyl isocyanate; 2-phenylcyclopropylisocyanate; benzylisocyanate; 2-ethylphenylisocyanate;benzoylisocyanate; meta and para-tolylisocyanate; 2-, 3-, or4-nitrophenylisocyanates; 2-ethoxyphenyl isocyanate; 3-methoxyphenylisocyanate; 4-methoxyphenylisocyanate; ethyl 4-isocyanatobenzoate;2,6-dimethylphenylisocyante; 1-naphthylisocyanate;(naphthyl)ethylisocyantes; and the like, as well as mixtures thereof.Examples of diisocyanates include isophorone diisocyanate (IPDI);toluene diisocyanate (TDI); diphenylmethane-4,4′-diisocyanate (MDI);hydrogenated diphenylmethane-4,4′-diisocyanate (H12MDI); tetra-methylxylene diisocyanate (TMXDI); hexamethylene-1,6-diisocyanate (HDI);hexamethylene-1,6-diisocyanate; naphthalene-1,5-diisocyanate;3,3′-dimethoxy-4,4′-biphenyldiisocyanate;3,3′-dimethyl-4,4-bimethyl-4,4′-biphenydiisocyanate; phenylenediisocyanate; 4,4′-biphenyldiisocyanate; trimethylhexamethylenediisocyanate; tetramethylene xylene diisocyanate;4,4′-methylenebis(2,6-diethylphenyl isocyanate);1,12-diisocyanatododecane; 1,5-diisocyanato-2-methylpentane;1,4-diisocyanatobutane; dimer diisocyanate and cyclohexylenediisocyanate and its isomers; uretidione dimers of HDI; and the like, aswell as mixtures thereof. Examples of triisocyanates or theirequivalents include the trimethylolpropane trimer of TDI, and the like,isocyanurate trimers of TDI, HDI, IPDI, and the like, and biuret trimersof TDI, HDI, IPDI, and the like, as well as mixtures thereof. Examplesof higher isocyanate functionalities include copolymers of TDI/HDI, andthe like, and MDI oligomers, as well as mixtures thereof.

Any suitable reaction condition for making urethane compounds bycondensing alcohols with isocyanates can be used to prepare theurethane-substituted compounds. Typically (although not necessarily),the reaction is carried out at elevated temperatures (for example, fromabout 60 to about 160° C.) in the presence of an optional urethanereaction catalyst, such as dibutyl tin dilaurate, bismuthtris-neodecanoate, cobalt benzoate, lithium acetate, stannous octoate,triethylamine, or the like. In a specific embodiment, the reactionconditions are conducted in an inert atmosphere, such as argon ornitrogen gas or other suitable gases, to prevent oxidizing or yellowingof the reaction products and to prevent undesirable side reactions. Thereaction can employ an inert solvent, such as toluene or the like, orcan be performed neat (i.e., without a solvent). The mole ratio ofreactants is adjusted so that the isocyanate functionalities arecompletely consumed in the reaction with a slight molar excess ofalcohol-substituted colorant typically remaining. The reactants can beadded together in any order and/or added to the reaction as physicalmixtures. If desired, reaction conditions and the order of the additionof reactants can be controlled for several reasons, such as to provide acontrolled exothermic reaction, to tailor the distribution of moleculesin the antioxidant-containing material, or the like. When doing theseadjustments, the different reactivities to isocyanates of alcoholsversus amines can be employed, as well as the different reactivities ofthe two separate isocyanate groups on IPDI. See, for example, J. H.Saunders and K. C. Frisch's “Polyurethanes Part I, Chemistry” publishedby Interscience of New York, N.Y. in 1962 and Olin Chemicals' LUXATE® IMisophorone diisocyanate technical product information sheet, thedisclosures of each of which are totally incorporated herein byreference, which provide further explanation of this chemistry.

Compounds of the formula

can be prepared by first preparing a urea-substituted precursor from adiamino compound by reacting the diamino compound with an isocyanate,either neat or, optionally, in the presence of a solvent, as follows:

Thereafter, the resulting urea precursor can be reacted with abrominated compound of the formula

by reacting the brominated starting material with the urea precursor inthe presence of a base and an optional catalyst and heating, as follows:

The diamino compound and the isocyanate are present in any desired oreffective relative amounts, in one embodiment at least about 0.85 moleof isocyanate group per every one mole of diamino compound, in anotherembodiment at least about 0.95 mole of isocyanate group per every onemole of diamino compound, and in yet another embodiment at least about0.99 mole of isocyanate group per every one mole of diamino compound,and in one embodiment no more than about 1.02 moles of isocyanate groupper every one mole of diamino compound, in another embodiment no morethan about 1.01 moles of isocyanate group per every one mole of diaminocompound, and in yet another embodiment no more than about 1.005 molesof isocyanate group per every one mole of diamino compound, although therelative amounts of diamino compound and isocyanate group can be outsideof these ranges.

The brominated starting material and the urea precursor are present inany desired or effective relative amounts, in one embodiment at leastabout 1 mole of urea precursor per every one mole of brominated startingmaterial, in another embodiment at least about 5 moles of urea precursorper every one mole of brominated starting material, and in yet anotherembodiment at least about 12 moles of urea precursor per every one moleof brominated starting material, and in one embodiment no more thanabout 20 moles of urea precursor per every one mole of brominatedstarting material, in another embodiment no more than about 15 moles ofurea precursor per every one mole of brominated starting material, andin yet another embodiment no more than about 13 moles of urea precursorper every one mole of brominated starting material, although therelative amounts of urea precursor and brominated starting material canbe outside of these ranges.

Any desired or effective base can be employed. Examples of suitablebases include (but are not limited to) sodium carbonate, potassiumcarbonate, calcium carbonate, calcium oxide, zinc oxide, and the like,as well as mixtures thereof. The base is present in any desired oreffective amount, in one embodiment at least about 0.5 mole of base perevery one mole of brominated starting material, in another embodiment atleast about 1 mole of base per every one mole of brominated startingmaterial, and in yet another embodiment at least about 2 moles of baseper every one mole of brominated starting material, and in oneembodiment no more than about 5 moles of base per every one mole ofbrominated starting material, in another embodiment no more than about 4moles of base per every one mole of brominated starting material, and inyet another embodiment no more than about 3 moles of base per every onemole of brominated starting material, although the relative amounts ofbase and brominated starting material can be outside of these ranges.

When an optional solvent is employed for the reaction between thebrominated starting material and the urea precursor, any desired oreffective solvent can be employed, such as xylene, toluene, benzene,chlorobenzene, nitrobenzene, dichlorobenzene, N-methylpyrrolidinone,dimethyl formamide, dimethyl sulfoxide, sulfolane, hexanol, octanol, orthe like, as well as mixtures thereof.

When an optional catalyst is employed, any desired or effective catalystcan be employed, including copper salts, such as cupric acetate, coppersulfate, copper II acetate monohydrate, copper powder, and the like, aswell as mixtures thereof.

The reaction mixture containing the brominated starting material, theurea precursor, the optional solvent, the base, and the optionalcatalyst is heated to any desired or effective temperature, typicallythe reflux temperature of the selected solvent, in one embodiment atleast about 100° C., and in one embodiment no more than about 200° C.,although the temperature can be outside of these ranges.

The reaction mixture is heated for any desired or effective period oftime, in one embodiment at least about 2 hours, and in anotherembodiment at least about 24 hours, and in one embodiment no more thanabout 72 hours, and in another embodiment no more than about 48 hours,although the heating time can be outside of these ranges.

The urea-substituted colorant compound can be recovered from thereaction mixture as a solid by filtration, followed by washing anddrying. If desired, purification can be carried out by filtration,redissolution in the solvent, heating, cooling, precipitating thecolorant from the solution, filtering, washing the colorant with asolvent such as methanol, ethanol, or the like, and repeating this cycleuntil thin layer chromatography of the collected solid indicates thatthere is no detectable unreacted reactant present in the solid.

Compounds of the formula

can be prepared from brominated compounds of the formula

by reacting the brominated starting material with the correspondingaminobenzene having the desired acid group of the formula —R₆COOH,generally with an excess of the aminobenzene adduct, either neat or,optionally, in the presence of a solvent, at elevated temperatures.Workup usually entails quenching in water if run neat or in a watersoluble solvent, filtering, washing, and drying, or if run in a waterinsoluble solvent, cooling and allowing the product to precipitatefollowed by filtering, washing, and drying. The reaction proceeds asfollows:

The brominated starting material and the aminobenzene are present in anydesired or effective relative amounts, in one embodiment at least about1 mole of aminobenzene per every one mole of brominated startingmaterial, in another embodiment at least about 5 moles of aminobenzeneper every one mole of brominated starting material, and in yet anotherembodiment at least about 12 moles of aminobenzene per every one mole ofbrominated starting material, and in one embodiment no more than about20 moles of aminobenzene per every one mole of brominated startingmaterial, in another embodiment no more than about 15 moles ofaminobenzene per every one mole of brominated starting material, and inyet another embodiment no more than about 13 moles of aminobenzene perevery one mole of brominated starting material, although the relativeamounts of aminobenzene and brominated starting material can be outsideof these ranges.

Any desired or effective base can be employed. Examples of suitablebases include (but are not limited to) sodium carbonate, potassiumcarbonate, calcium carbonate, calcium oxide, zinc oxide, and the like,as well as mixtures thereof. The base is present in any desired oreffective amount, in one embodiment at least about 0.5 mole of base perevery one mole of brominated starting material, in another embodiment atleast about 1 mole of base per every one mole of brominated startingmaterial, and in yet another embodiment at least about 2 moles of baseper every one mole of brominated starting material, and in oneembodiment no more than about 5 moles of base per every one mole ofbrominated starting material, in another embodiment no more than about 4moles of base per every one mole of brominated starting material, and inyet another embodiment no more than about 3 moles of base per every onemole of brominated starting material, although the relative amounts ofaniline and brominated starting material can be outside of these ranges.

Optionally, if desired, a catalyst for the reaction can be employed,such as a copper salt, including (but not limited to) cupric acetate,copper sulfate, copper II acetate monohydrate, copper powder, and thelike, in any desired or effective amount.

While not required, if desired, an optional solvent can be employed. Ifused, any desired or effective solvent can be used, including polaraprotic solvents such as N-methylpyrrolidinone, dimethyl formamide,dimethyl sulfoxide, sulfolane, or the like, as well as mixtures thereof,in any desired or effective amount, in one embodiment in a ratio byweight of at least about 1 part by weight brominated starting materialper every hundred parts by weight solvent, and in one embodiment in aratio by weight of no more than about 20 parts by weight brominatedstarting material per every hundred parts by weight solvent, althoughthe relative amounts of solvent and brominated starting material can beoutside of these ranges.

The reaction mixture containing the aminobenzene and the brominatedstarting material is heated to any desirable or effective temperature toeffect the reaction, in one embodiment at least about 100° C., inanother embodiment at least about 120° C., and in yet another embodimentat least about 180° C., and in one embodiment no more than about 250°C., in another embodiment no more than about 200° C., and in yet anotherembodiment no more than about 190° C., although the temperature can beoutside of these ranges.

The reaction between the aminobenzene and the brominated startingmaterial is allowed to proceed for any desired or effective period oftime, in one embodiment at least about 10 minutes, in another embodimentat least about 1 hour, and in yet another embodiment at least about 1.5hour, and in one embodiment no more than about 4 days, in anotherembodiment no more than about 1 day, and in yet another embodiment nomore than about 2 hours, although the reaction time can be outside ofthese ranges.

Upon completion of the reaction, the compound of the formula

can be recovered by quenching the reaction mixture with a mixture ofacid and water, followed by filtration, washing, and drying. Any desiredor effective acid can be employed, such as hydrochloric acid, sulfuricacid, phosphoric acid, or the like, as well as mixtures thereof, in anydesired or effective concentration, in one specific embodiment at leastabout 1 percent by weight acid in water, and in one specific embodimentno more than about 20 percent by weight acid in water, although theconcentration can be outside of these ranges.

The acid-substituted compound of the formula

can be converted to an ester-substituted compound of the formula

by reacting the acid-substituted compound with an alcohol of the formulaR₇—OH, an optional solvent, and an optional esterification catalyst andheating, as follows:

The acid-substituted compound and the alcohol are present in any desiredor effective relative amounts, in one embodiment at least about 1 moleof alcohol per every one mole of acid-substituted compound, in anotherembodiment at least about 1.05 moles of alcohol per every one mole ofacid-substituted compound, and in yet another embodiment at least about1.1 moles of alcohol per every one mole of acid-substituted compound,and in one embodiment no more than about 2 moles of alcohol per everyone mole of acid-substituted compound, in another embodiment no morethan about 1.5 moles of alcohol per every one mole of acid-substitutedcompound, and in yet another embodiment no more than about 1.25 moles ofalcohol per every one mole of acid-substituted compound, although therelative amounts of acid-substituted compound and alcohol can be outsideof these ranges.

When the optional esterification catalyst is present, any desired oreffective esterification catalyst can be used, such as para-toluenesulfonic acid, dibutyl tin dilaurate, or the like, as well as mixturesthereof. The esterification catalyst is present in any desired oreffective amount, in one embodiment at least about 0.05 mole ofesterification catalyst per every one mole of alcohol, and in oneembodiment no more than about 0.5 mole of esterification catalyst permole of alcohol, although the amount of esterification catalyst can beoutside of these ranges.

When present, any desired or effective solvent can be used. Examples ofsuitable solvents include xylene, toluene, benzene, chlorobenzene,nitrobenzene, dichlorobenzene, and the like, as well as mixturesthereof. When the optional solvent is used, the reactants are present inthe solvent in any desired or effective amount, in one embodiment atleast about 25 grams of alcohol per every one liter of solvent, inanother embodiment at least about 50 grams of alcohol per every oneliter of solvent, and in yet another embodiment at least about 100 gramsof alcohol per every one liter of solvent, and in one embodiment no morethan about 200 grams of alcohol per every one liter of solvent, inanother embodiment no more than about 150 grams of alcohol per every oneliter of solvent, and in yet another embodiment no more than about 100grams of alcohol per every one liter of solvent, although the amount ofsolvent can be outside of these ranges.

The reaction mixture containing the alcohol, the acid-substitutedcompound, the optional solvent, and the optional esterification catalystis heated to any desirable or effective temperature, typically thereflux temperature of the selected solvent, in one embodiment at leastabout 100° C., and in one embodiment no more than about 130° C.,although the temperature can be outside of these ranges.

The reaction mixture containing the alcohol, the acid-substitutedcompound, the optional solvent, and the optional esterification catalystis heated for any desirable or effective period of time, in oneembodiment at least about 2 hours, in another embodiment at least about24 hours, and in one embodiment no more than about 72 hours, and inanother embodiment no more than about 48 hours, although the heatingtime can be outside of these ranges.

The esterified compound can be recovered from the reaction mixture as asolid by filtration, followed by washing and drying. If desired,purification can be carried out by filtration, redissolution in thesolvent, heating, cooling, precipitating the colorant from the solution,filtering, washing the compound with a solvent such as methanol,ethanol, or the like, and repeating this cycle until thin layerchromatography of the collected solid indicates that there is nodetectable unreacted reactant present in the solid.

The acid-substituted compound of the formula

can be converted to an amide-substituted compound of the formula

by reacting the acid-substituted compound with an amine of the formulaR₇—NH₂, an optional solvent, and an optional amidification catalyst andheating, as follows:

The acid-substituted compound and the amine are present in any desiredor effective relative amounts, in one embodiment at least about 1 moleof amine per every one mole of acid-substituted compound, in anotherembodiment at least about 1.05 moles of amine per every one mole ofacid-substituted compound, and in yet another embodiment at least about1.1 moles of amine per every one mole of acid-substituted compound, andin one embodiment no more than about 2 moles of amine per every one moleof acid-substituted compound, in another embodiment no more than about1.5 moles of amine per every one mole of acid-substituted compound, andin yet another embodiment no more than about 1.25 moles of amine perevery one mole of acid-substituted compound, although the relativeamounts of acid-substituted compound and amine can be outside of theseranges.

When the optional amidification catalyst is present, any desired oreffective amidification catalyst can be used, such as phosphoric acid orthe like. The amidification catalyst is present in any desired oreffective amount, in one embodiment at least about 0.05 mole ofamidification catalyst per every one mole of amine, and in oneembodiment no more than about 0.5 mole of amidification catalyst permole of amine, although the amount of amidification catalyst can beoutside of these ranges.

When present, any desired or effective solvent can be used. Examples ofsuitable solvents include xylene, toluene, benzene, chlorobenzene,nitrobenzene, dichlorobenzene, and the like, as well as mixturesthereof. When the optional solvent is used, the reactants are present inthe solvent in any desired or effective amount, in one embodiment atleast about 25 grams of amine per every one liter of solvent, in anotherembodiment at least about 50 grams of amine per every one liter ofsolvent, and in yet another embodiment at least about 100 grams of amineper every one liter of solvent, and in one embodiment no more than about200 grams of amine per every one liter of solvent, in another embodimentno more than about 150 grams of amine per every one liter of solvent,and in yet another embodiment no more than about 100 grams of amine perevery one liter of solvent, although the amount of solvent can beoutside of these ranges.

The reaction mixture containing the amine, the acid-substitutedcompound, the optional solvent, and the optional amidification catalystis heated to any desirable or effective temperature, typically thereflux temperature of the selected solvent, in one embodiment at leastabout 100° C., and in one embodiment no more than about 200° C.,although the temperature can be outside of these ranges.

The reaction mixture containing the amine, the acid-substitutedcompound, the optional solvent, and the optional amidification catalystis heated for any desirable or effective period of time, in oneembodiment at least about 2 hours, in another embodiment at least about24 hours, and in one embodiment no more than about 72 hours, and inanother embodiment no more than about 48 hours, although the heatingtime can be outside of these ranges.

The amidified compound can be recovered from the reaction mixture as asolid by filtration, followed by washing and drying. If desired,purification can be carried out by filtration, redissolution in thesolvent, heating, cooling, precipitating the colorant from the solution,filtering, washing the colorant with a solvent such as methanol,ethanol, or the like, and repeating this cycle until thin layerchromatography of the collected solid indicates that there is nodetectable unreacted reactant present in the solid.

The acid-substituted compound of the formula

can also be converted to an amide-substituted compound of the formula

by reacting the acid-substituted compound with an isocyanate of theformula R₇—NCO, optionally in the presence of a catalyst, either neator, optionally, in the presence of a solvent, at elevated temperaturesas follows:

The carboxylic acid-substituted compound and the isocyanate are presentin any desired or effective relative amounts, in one embodiment at leastabout 1 mole of isocyanate group per every one mole of carboxylicacid-substituted compound, in another embodiment at least about 1.05moles of isocyanate group per every one mole of carboxylicacid-substituted compound, and in yet another embodiment at least about1.1 moles of isocyanate group per every one mole of carboxylicacid-substituted compound, and in one embodiment no more than about 2moles of isocyanate group per every one mole of carboxylicacid-substituted compound, in another embodiment no more than about 1.5moles of isocyanate group per every one mole of carboxylicacid-substituted compound, and in yet another embodiment no more thanabout 1.25 moles of isocyanate group per every one mole of carboxylicacid-substituted compound, although the relative amounts of carboxylicacid-substituted compound and isocyanate group can be outside of theseranges.

When the optional catalyst is present, any desired or effective catalystcan be used, such as dibutyl tin dilaurate or the like. The catalyst ispresent in any desired or effective amount, in one embodiment at leastabout 0.05 mole of catalyst per every one mole of isocyanate, and in oneembodiment no more than about 0.5 mole of catalyst per mole ofisocyanate, although the amount of catalyst can be outside of theseranges.

When present, any desired or effective aprotic solvent can be used.Examples of suitable solvents include xylene, toluene, benzene,chlorobenzene, nitrobenzene, dichlorobenzene, and the like, as well asmixtures thereof. When the optional solvent is used, the reactants arepresent in the solvent in any desired or effective amount, in oneembodiment at least about 25 grams of isocyanate per every one liter ofsolvent, in another embodiment at least about 50 grams of isocyanate perevery one liter of solvent, and in yet another embodiment at least about100 grams of isocyanate per every one liter of solvent, and in oneembodiment no more than about 200 grams of isocyanate per every oneliter of solvent, in another embodiment no more than about 150 grams ofisocyanate per every one liter of solvent, and in yet another embodimentno more than about 100 grams of isocyanate per every one liter ofsolvent, although the amount of solvent can be outside of these ranges.

The reaction mixture containing the isocyanate, the carboxylicacid-substituted compound, the optional solvent, and the optionalcatalyst is heated to any desired or effective temperature, typicallythe reflux temperature of the selected solvent, in one embodiment atleast about 100° C., and in one embodiment no more than about 200° C.,although the temperature can be outside of these ranges.

The reaction mixture containing the isocyanate, the carboxylicacid-substituted compound, the optional solvent, and the optionalcatalyst is heated for any desired or effective period of time, in oneembodiment at least about 2 hours, and in another embodiment at leastabout 24 hours, and in one embodiment no more than about 72 hours, andin another embodiment no more than about 48 hours, although the heatingtime can be outside of these ranges.

The amide-substituted compound can be recovered from the reactionmixture as a solid by filtration, followed by washing and drying. Ifdesired, purification can be carried out by filtration, redissolution inthe solvent, heating, cooling, precipitating the colorant from thesolution, filtering, washing the colorant with a solvent such asmethanol, ethanol, or the like, and repeating this cycle until thinlayer chromatography of the collected solid indicates that there is nodetectable unreacted reactant present in the solid.

Specific embodiments will now be described in detail. These examples areintended to be illustrative, and the claims are not limited to thematerials, conditions, or process parameters set forth in theseembodiments. All parts and percentages are by weight unless otherwiseindicated.

EXAMPLE I

To a 500 milliliter round bottom flask with stir magnet was charged 250grams of 4-aminophenethyl alcohol (obtained from Aceto Corporation, LakeSuccess, N.Y.) and 15.6 grams of sodium carbonate (obtained from AldrichChemical Co., Milwaukee, Wis.). The mixture was heated to 140° C. in anoil bath with stirring. After the mixture was molten, 50 grams of4-bromo-1,9-N-methyl anthrapyridone (obtained from Hangsu Aolunda HighTech Industry Co. Ltd., Shanghai, China) was added and the temperatureof the oil bath was increased to 185° C. while stirring was continued.After 1 hour, the reaction mixture was quenched into 1,500 millilitersof a 0.5 percent solution of HCl in water while stirring. After severalhours, the solids were collected by vacuum filtration and washed twoadditional times in HCl/H₂O, filtering after each wash. The filtrant (abrown solution) decreased in color as each subsequent wash wasperformed. The solids were collected and dried in a vacuum oven at 60°C. The spectral strength of the product was determined using aspectrophotographic procedure based on the measurement of the product insolution by dissolving the product in toluene and measuring theabsorbance using a Perkin Elmer Lambda 2S UV/VIS spectrophotometer. Thespectral strength of the product was measured as about 28,552 mLAbsorbance Units per gram at absorption λ_(max), 544 nanometers. Thehydroxyethyl substituted product was believed to be of the formula

EXAMPLE II

To a 1 liter flask with stir magnet was charged 50 grams of thehydroxyethyl substituted product prepared in Example I, 137.6 grams ofUNILIN 700 (a long chain fatty alcohol believed to be of the formulaCH₃(CH₂)_(n)OH wherein n represents an average number having an averagevalue of about 47 and is believed to have a range of from about 30 toabout 70, obtained from Baker Petrolite Corp., Sugarland, Tex.), 400grams of xylene (obtained from Aldrich Chemical Co.), and 2 grams ofp-toluene sulfonic acid (obtained from Aldrich Chemical Co.). The flask,equipped with a Dean-Stark trap and condenser, was placed in an oil bathat 150° C. and allowed to reflux for 4 days. The reaction product wasthen poured into a 1 liter beaker and allowed to cool and precipitate.The solids were then filtered, collected, and triturated in methanol(about 500 milliliters), followed by refiltering and repeating theprocess three times. The solids were then dried overnight in a vacuumoven at 60° C. The spectral strength of the product was determined usinga spectrophotographic procedure based on the measurement of the productin solution by dissolving the product in a 1:1 mixture oftetrahydrofuran and toluene and measuring the absorbance using a PerkinElmer Lambda 2S UV/VIS spectrophotometer. The spectral strength of theproduct was measured as about 8,921 mL Absorbance Units per gram atabsorption λ_(max), 543 nanometers. The C50 ester substituted productwas believed to be of the formula

wherein n represents an average number and has an average value of about47 and is believed to have a range of from about 30 to about 70.

EXAMPLE III

To a 125 milliliter flask with stir magnet was charged 15.1 grams of thehydroxyethyl substituted product prepared in Example I, 11.9 grams ofPRIPOL® dimer acid (a dimer diol believed to be of the formulaHOOC—C₃₆H_(64+n)—COOH wherein C₃₆H_(64+n) was a branched alkylene groupwhich may include unsaturations and cyclic groups, wherein n is aninteger of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and wherein one isomerthereof was believed to be of the formula

obtained from Uniqema, New Castle, Del.), 52.5 grams of xylene (obtainedfrom Aldrich Chemical Co.), and 0.1 grams of p-toluene sulfonic acid(obtained from Aldrich Chemical Co.), The flask, equipped with aDean-Stark trap and condenser, was placed in an oil bath at 150° C. andallowed to reflux for 4 days. The reaction product was then poured intoa 1 liter beaker and allowed to cool and precipitate. The solids werethen filtered, collected, and triturated in methanol (about 500milliliters), followed by refiltering and repeating the process threetimes. The solids were then dried overnight in a vacuum oven 60° C. Theproduct was believed to be of the formula

wherein C₃₆H_(64+n) was a branched alkylene group which may includeunsaturations and cyclic groups, wherein n is an integer of 0, 1, 2, 3,4, 5, 6, 7, 8, 9, or 10, and wherein one isomer thereof was believed tobe of the formula

EXAMPLE IV

To a 250 milliliter flask with stir magnet was charged 15.1 grams of thehydroxyethyl substituted product prepared in Example I, 11.4 grams ofDimer Diisocyanate 1410 (a dimer diisocyanate believed to be of theformula HOOC—C₃₆H_(64+n)—COOH wherein C₃₆H_(64+n) was a branchedalkylene group which may include unsaturations and cyclic groups,wherein n is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, andwherein one isomer thereof was believed to be of the formula

obtained from Cognis Corp, Cincinnati, Ohio), 129.7 grams of xylene(obtained from Aldrich Chemical Co.), and 2 drops of FASCAT 4202catalyst (obtained from Elf Atochem North America Inc., Philadelphia,Pa.). The flask, equipped with a condenser, was placed in an oil bath at155° C. and allowed to reflux for 5 hours. An infrared spectrum of thereaction was taken to ensure that no isocyanate reactant remained andthat the reaction was complete. The reaction product was then pouredinto 1,500 milliliters of methanol and allowed to cool and precipitate.The solids were then filtered, collected, and triturated in methanol(about 500 milliliters), followed by refiltering and repeating theprocess three times. The solids were then dried overnight in a vacuumoven at 60° C. The product was believed to be of the formula

wherein C₃₆H_(64+n) was a branched alkylene group which may includeunsaturations and cyclic groups, wherein n is an integer of 0, 1, 2, 3,4, 5, 6, 7, 8, 9, or 10, and wherein one isomer thereof was believed tobe of the formula

EXAMPLE V

To a 500 milliliter round bottom flask equipped with stir magnet ischarged 275 grams of p-aminophenylacetic acid (available from TCIAmerica, Portland Oreg.) and 15.6 grams of sodium carbonate (availablefrom Aldrich Chemical Co., Milwaukee, Wis.). The mixture is heated to140° C. in an oil bath with stirring. After the mixture is molten, 50grams of 4-bromo-1,9-N-methyl anthrapyridone (available from HangsuAolunda High Tech Industry Co. Ltd., Shanghai, China) is added and thetemperature of the oil bath is increased to 185° C. while stirring iscontinued. After 1 hour, the reaction mixture is quenched into 1,500milliliters of 5 percent HCl in water while stirring. After severalhours, the solids are collected by vacuum filtration and washed twoadditional times in HCl/H₂O, filtering after each wash. The solids arecollected and dried in a vacuum oven at 60° C. It is believed that theproduct will be of the formula

EXAMPLE VI

To a 1 liter flask with stir magnet is charged 55.1 grams of thephenylacetic acid substituted product prepared in Example V, 137.6 gramsof UNICID 700 (a long chain fatty acid believed to be of the formulaCH₃(CH₂)₄₆COOH, available from Baker Petrolite Corp., Sugarland, Tex.),400 grams of xylene (available from Aldrich Chemical Co.), and 2 gramsof p-toluene sulfonic acid (available from Aldrich Chemical Co.). Theflask, equipped with a Dean-Stark trap and condenser, is placed in anoil bath at 150° C. and allowed to reflux for 4 days. The reactionproduct is then poured into a 1 liter beaker and allowed to cool andprecipitate. The solids are then filtered, collected, and triturated inmethanol (about 500 milliliters), followed by refiltering and repeatingthe process three times. The solids are then dried overnight in a vacuumoven at 60° C. It is believed that the product will be of the formula

EXAMPLE VII

To a 250 milliliter round bottom flask equipped with magnetic stir baris added 5 grams of the compound formed in Example V, 7.6 grams ofoctadecyl amine (ARMEEN 18 D, available from Akzo Nobel Chemicals Inc.,McCook, Ill.), and 70 grams of xylene. The flask is placed understirring and a condenser and Dean Stark trap in a hot oil bath at 150°C. for 48 hours. Thin layer chromatography (TLC) by normal phase in 10percent methanol in toluene is used to determine reaction completion.Thereafter, the solvent is distilled off and the product is collected.It is believed that the product will be of the formula

EXAMPLE VIII

To a 250 milliliter round bottom flask equipped with magnetic stir baris added 5 grams of the compound formed in Example V, 7.6 grams ofoctadecyl isocyanate (Mondur O, available from Bayer Corp., Pittsburgh,Pa.), 2 drops of FASCAT 4202 catalyst (available from Elf Atochem NorthAmerica Inc., Philadelphia, Pa.) and 70 grams of xylene. The flask isplaced under stirring and a condenser and Dean Stark trap in a hot oilbath at 150° C. for 5 hours. Thin layer chromatography (TLC) by normalphase in 10 percent methanol in toluene is used to determine reactioncompletion. Thereafter, the solvent is distilled off and the product iscollected. It is believed that the product will be of the formula

EXAMPLE IX

To a 250 milliliter round bottom flask in an oil bath with stir magnetis charged 10.2 grams of octadecyl amine (available from AldrichChemicals), 10.6 grams of sodium carbonate (available from AldrichChemical Co.), 150 milliliters of 2-methylpyrrolidinone (available fromAldrich Chemical Co.), 0.2 grams of copper II acetate (available fromAldrich Chemical Co.), and 33.9 grams of 4-bromo-1,9-N-methylanthrapyridone (available from Hangsu Aolunda High Tech Industry Co.Ltd., Shanghai, China), and the temperature of the oil bath is increasedto 150° C. while stirring is maintained for 16 hours. The reactionmixture is then quenched into 500 milliliters of methanol. The resultingsolid product is then filtered, collected, and triturated in methanol(about 500 milliliters), followed by refiltering and repeating theprocess three times. The solid is then dried overnight in a vacuum ovenat 60° C. It is believed that the product will be of the formula

EXAMPLE X

To a 250 milliliter round bottom flask with stir magnet is charged 13.6grams of 2-(aminophenyl)ethylamine (available from Aldrich Chemical Co.)and 150 milliliters of dry 2-methylpyrrolidinone (available from AldrichChemical Co.) under a nitrogen blanket with stirring. 29.6 grams ofoctadecylisocyanate (Mondur O, available from Bayer Corp. of Pittsburgh,Pa.) is then slowly added over 15 minutes. Normally an exotherm isobserved as the reaction of an isocyanate and aliphatic primary amine isquite exothermic. Heat is applied so as to keep the reaction mixture insolution. The reaction progress is followed by FTIR analysis as the NCOpeak (approx. 2250 cm⁻¹) disappears as the isocyanate is consumed. Themixture is then heated to 140° C. and 33.9 grams of 4-bromo-1,9-N-methylanthrapyridone (available from Hangsu Aolunda High Tech Industry Co.Ltd., Shanghai, China) and 0.2 grams of copper II acetate (availablefrom Aldrich Chemical Co.) are added and the reaction is continued for16 hours. Thereafter, the reaction mixture is quenched into 500milliliters of methanol. The resulting solid product is then filtered,collected, and triturated in methanol (about 500 milliliters), followedby refiltering and repeating the process three times. The solid is thendried overnight in a vacuum oven at 60° C. It is believed that theproduct will be of the formula

EXAMPLE XI

To a 500 milliliter round bottom flask with stir magnet was charged 10.2grams of dodecyl aniline (obtained from EMS Dottikon AG, Montvale, N.J.)and 0.3 grams of sodium carbonate (obtained from Aldrich Chemicals). Themixture was heated to 140° C. in an oil bath with stirring. After themixture was molten, 1.0 grams of 4-bromo-1,9-N-methyl anthrapyridone(obtained from Hangsu Aolunda High Tech Industry Co. Ltd., Shanghai,China) was added and the temperature of the oil bath was increased to185° C. while stirring was continued. After 1 hour, the reaction mixturewas quenched into 450 milliliters of 5 percent HCl in water. The crudeproduct, a viscous liquid, was dissolved in 250 milliliters of toluene,placed in a 1 liter separatory funnel, and washed with 450 millilitersof 5 percent HCl. The toluene layer containing the purified product wastransferred to a 1 liter round bottom flask and placed on a rotaryevaporator and the toluene was distilled off, leaving the product. Theproduct was believed to be of the formula

EXAMPLE XII

To a 500 milliliter round bottom flask with stir magnet is charged 250grams of 3-aminopropyl diethyleneglycol (DCA 163, available from DixieChemical Co., Pasadena, Tex.) and 15.6 grams of sodium carbonate(available from Aldrich Chemical Co., Milwaukee, Wis.). The mixture isheated to 140° C. in an oil bath with stirring. When the mixture ismolten, 50 grams of 4-bromo-1,9-N-methyl anthrapyridone (available fromHangsu Aolunda High Tech Industry Co. Ltd., Shanghai, China) is addedand the temperature of the oil bath is increased to 185° C. whilestirring is continued. After 1 hour, the reaction mixture is quenchedinto 1,500 milliliters of a 0.5 percent solution of HCl in water whilestirring. After several hours, the solids are collected by vacuumfiltration and washed two additional times in HCl/H₂O, filtering aftereach wash. It is believed that the product will be of the formula

EXAMPLE XIII

To a 150 milliliter round bottom flask equipped with magnetic stir baris added 5 grams of the compound formed in Example XII, 3.5 grams ofoctadecyl isocyanate (Mondur O, available from Bayer Corp., Pittsburgh,Pa.), 2 drops of FASCAT 4202 catalyst (available from Elf Atochem NorthAmerica Inc., Philadelphia, Pa.) and 70 grams of xylene. The flask isplaced under stirring and a condenser and Dean Stark trap in a hot oilbath at 150° C. for 5 hours. The solvent is distilled off and theproduct is collected. It is believed that the product will be of theformula

EXAMPLE XIV

An ink base was prepared by melting, admixing, and filtering thefollowing ingredients:

polyethylene wax (PE 655, obtained from Baker Petrolite, Tulsa, Okla.,of the formula CH₃(CH₂)₅₀CH₃), 42.01 parts by weight;

stearyl stearamide wax (KEMAMIDE® S-180, obtained from CromptonCorporation, Greenwich, Conn.), 18.82 parts by weight;

tetra-amide resin obtained from the reaction of one equivalent of a C-36dimer acid obtained from Uniqema, New Castle, Del. with two equivalentsof ethylene diamine and UNICID® 700 (obtained from Baker Petrolite,Tulsa, Okla., a long chain hydrocarbon having a terminal carboxylic acidgroup), prepared as described in Example 1 of U.S. Pat. No. 6,174,937,the disclosure of which is totally incorporated herein by reference,24.99 parts by weight;

urethane resin obtained from the reaction of two equivalents of ABITOL®E hydroabietyl alcohol (obtained from Hercules Inc., Wilmington, Del.)and one equivalent of isophorone diisocyanate, prepared as described inExample 1 of U.S. Pat. No. 5,782,966, the disclosure of which is totallyincorporated herein by reference, 8.82 parts by weight;

urethane resin that is the adduct of three equivalents of stearylisocyanate and a glycerol-based alcohol, prepared as described inExample 4 of U.S. Pat. No. 6,309,453, the disclosure of which is totallyincorporated herein by reference, 5.21 parts by weight; and

NAUGUARD® 445 antioxidant (available from Uniroyal Chemical Co.,Middlebury, Conn.), 0.15 parts by weight.

Thereafter, 566.4 grams of the ink carrier and 15.0 grams of thecolorant prepared in Example II (2.58 percent by weight) were added to a1 liter beaker and heated in an oven at 135° C. until molten.Subsequently, the beaker was inserted into a heating mantle set to 135°C. and the contents of the beaker were stirred for 45 minutes. Theresulting ink was then filtered through a combination of Whatman #3 and0.2 micron NAE filters and placed in a Mott filter assembly. Filtrationwas supported by the addition of 1 percent by weight FILTER-AID,obtained from Fluka Chemika, Switzerland, and proceeded at a temperatureof 135° C. until complete after 6 hours. The dynamic viscosity of theinks was measured using a stress-controlled Dynamic Stress Rheometer(DSR) 2000 from Rheometric Scientific (now TA Instruments). Geometry was40 mm diameter Cone and Plate. A stress of 1 Pascal was constantlymaintained during a step-stress experiment, and viscosity data pointswere gathered at an approximate rate of 0.5 points per second. Eachmeasurement lasted approximately 5 minutes, with an equilibration periodof about 80 seconds; subsequently, data measured between 100 and 300seconds were averaged. The dynamic viscosity of this ink at 140° C. was10.80 milliPascal seconds. The spectral strength of the ink wasdetermined using a spectrophotographic procedure based on themeasurement of the ink in solution by dissolving the ink in toluene andmeasuring the absorbance using a Perkin Elmer Lambda 2S UV/VISspectrophotometer. The spectral strength of this ink was measured asabout 105 mL Absorbance Units per gram at absorption λ_(max) of 543nanometers.

EXAMPLE XV

The procedure of Example XIV was repeated except that the amounts of theink ingredients (weight percent) were changed as follows:

-   -   polyethylene wax: 40.77    -   stearyl stearamide: 18.27    -   tetra-amide resin: 22.64    -   first urethane resin: 8.00    -   second urethane resin: 4.72    -   antioxidant. 0.13    -   colorant: 5.47        The dynamic viscosity of this ink at 140° C. was 10.70        milliPascal seconds. The spectral strength of this ink was        measured as about 301 mL Absorbance Units per gram at absorption        λ_(max) of 543 nanometers. The ink was then cast into ink sticks        and allowed to solidify.

COMPARATIVE EXAMPLE A

The procedure of Example XIV was repeated except that an anthraquinonecolorant prepared as described in Example 2 of U.S. Pat. No. 6,395,078,the disclosure of which is totally incorporated herein by reference, wasused instead of the colorant prepared in Example II and except that theamounts of the ink ingredients (weight percent) were changed as follows:

-   -   polyethylene wax: 41.11    -   stearyl stearamide: 18.41    -   tetra-amide resin: 25.55    -   first urethane resin: 8.63    -   second urethane resin: 5.10    -   antioxidant: 0.15    -   colorant: 1.04        The ink thus prepared was cast into ink sticks and allowed to        solidify. The dynamic viscosity of this ink at 140° C. was 10.61        mPas. The spectral strength of this ink was measured as about        239 mL Absorbance Units per gram at absorption λ_(max) of 533        nanometers.

Thermal Analysis

Thermal analysis of the inks from Example XV and Comparative Example Awas carried out by means of Dynamic Mechanical Analysis (DMA) using aRSA II Solids Analyzer (obtained from Rheometric Scientific) andDifferential Scanning Calorimetry (DSC) using a DSC 2920 (obtained fromTA Instruments). Dual-cantilever DMA analysis was carried out to measuremechanical properties of the ink samples, such as modulus of elasticity(e.g. Young's Modulus, E), or loss-angle tangent (which is defined to beLoss Modulus E″, divided by Storage Modulus E′), usually as functions offrequency. The measurement can be conducted at different temperatures,which makes it a useful tool in the thermo-mechanical analysis of anink. In preparation of the measurement, the ink is cast into thin sticksor rods. Each specimen is subsequently inserted into the instrument insuch a way that the two ends of the rod rest on a fork-shaped toolconnected with a load cell, while a thin tool touches the rod in itscenter. The upper tool is moved by a special type of actuator with aconstant frequency, and the lower tool measures the response of thesolid ink material. As a result, the loss angle tangent is measured as afunction of temperature. Maxima of this curve can be associated withglass transition temperatures in many cases, and the areas under themaxima of the same curve are a relative measure of sample toughness(high values indicating high toughness). Both values are reported forthe ink samples from Example XII and Comparative Example A in the tablebelow.

DSC is a well-known method of thermal analysis, done in a special kindof calorimeter, which in case of a calibrated measurement system is ableto determine the heat capacity of a sample by comparing it with areference. If this calibration is lacking, the method is still ofsignificant analytical use, since it permits the measurement of any heateffects in the sample specimen. In the case of inks, the method can beused to determine heats of fusion (or solidification) and temperatureswhich are associated with these phase-transition processes. The typicalheat flow curve of a phase transition shows one or several maxima(peaks), The temperature of the crossover point of the baseline with theleft-flank tangent line of a peak (for heating experiments) is reportedas an “onset” temperature T_(m(onset)) of the fusing process. In thecase that such a tangent line cannot be readily determined (e.g. severalbroad, fused maxima of the curve), we have instead reported thetemperatures of the peak maxima T_(m(max)) in the table. In addition,the specific heat of fusion ΔH_(m) (in J/g) was calculated byintegration of the area under the peak. Since glass transitions manifestthemselves as step-shaped patterns in heat capacity-temperature (orheat-flow-temperature) curves, DSC offers a convenient way to determinean estimate for glass transition temperatures and intervals. In thetable, the temperature of the point of inflection of such a step-shapedcurve is reported as glass transition temperature T_(g). The resultswere as follows:

Comparative Ink A Example XV Ink DSC T_(g) 8° C. 12° C. T_(m1(onset))76.2° C. 75.3° C. T_(m1(max)) 85.7° C. 85.2° C. T_(m2(max)) 106° C. 106°C. ΔH_(m)(Jg⁻¹) 177.0 179.5 DMA T_(g) (according to tan δ) 8° C. 15° C.Area under log(tan δ)  18.3  15.6These calorimetric data indicate that the inks will exhibit very similartransfix properties. The increase in glass transition temperature isconfirmed by dual-cantilever Dynamic Mechanical Analysis. The slightlyreduced area under the log(tan δ) curve indicates a simultaneousincrease in brittleness. It is believed that this change was not causedby the colorant but by the slightly reduced content of the secondurethane resin, which can act as a toughening agent.

Print Performance: Tape Diffusion

The inks prepared in Example XV and Comparative Example A were eachincorporated into different reservoirs of the printhead of a XEROX®PHASER® 850 phase change ink jet printer and used to generate prints ofdifferent text sizes and resolutions onto HAMMERMILL LASERPRINT® paper.The resulting prints were then partially covered with SCOTCH® brandtransparent tape. Some prints were maintained at room temperature andother prints were maintained at 60° C. After 5 days, the prints wereinspected. Whereas the characters generated with the Comparative ExampleA ink and maintained at 60° C. appeared blurred, the charactersgenerated with the Example XV ink and maintained at 60° C. were clearlylegible.

To assess the result of this test in numbers, a comparative qualitativescale ranging from −3.0 to +3.0 was defined. On this scale, negativevalues indicated undesirable performance and inferiority with respect tothe reference sample (that of Comparative Example A, which by itselftherefore was rated to be ±0.0), and positive values indicated adesirable performance and hence superiority with respect to thereference sample. For the purpose of number assessment, all charactersizes and print resolutions of the text were combined. A 5-day exposureto 60° C. (accelerated test) led to a comparative subjective rating of+2.5 for the prints generated with the ink of Example XV. In comparison,the diffusion process was significantly slower at room temperature,which immediately after the end of the 5-day test led to a lowercomparative subjective rating. By estimate, this rating value waslocated between +0.5 and +1.0 for a 5-day room temperature exposure. Thesamples were then kept in storage in a dark location at room temperaturefor another 2¼ years. An inspection of the samples after this timeperiod showed that the room temperature sample of the reference wastotally blurred and illegible, whereas the sample with the ink fromExample XV appeared virtually unchanged and legible, increasing itscomparative subjective rating to a value very close to +3.0.

Print Performance: Showthrough Diffusion

One disadvantage of some magenta colorants is their relatively rapiddiffusion through paper, resulting in discoloration of the rear side ofthe paper over time. The inks prepared in Example XV and ComparativeExample A were each incorporated into different reservoirs of theprinthead of a XEROX® PHASER® 850 phase change ink jet printer and usedto generate solid fill prints onto HAMMERMILL LASERPRINT® paper. Astandard resolution of 355×464 dpi was applied. Shortly after printing,the rear sides of the printed papers were scanned with an ACSPhotometer, and the respective L*a*b* coordinates were recorded.Thereafter, some of the prints were maintained at room temperature andsome of the prints were maintained at 60° C. In defined time intervalsof approximately 1 day, 3 days, 5 days, 10 days, and 30 days as reportedin the tables, the same sites on the rear sides of the printed paperswere again scanned for their color values, and decolorations werequantified by calculating the ΔE values with respect to the initialscan. To different degrees in different parts of the visible lightspectrum, color differences with ΔE values exceeding 1.0 are perceptibleto the eye of the average observer. Low ΔE values are desirable. Theresults were as follows:

a)Room Temperature:

Comparative Example A Example XV Time (Days) □E Time (Days) □E 0.00 0.000.00 0.00 1.02 0.05 0.88 0.09 2.00 0.22 2.93 0.09 4.72 0.66 5.09 0.148.77 1.59 9.86 0.13 27.99 5.19 32.87 0.39b) 60° C.:

Comparative Example A Example XV Time (Days) □E Time (Days) □E 0.00 0.000.00 0.00 1.02 1.88 0.88 0.44 2.00 4.60 2.93 0.49 4.72 7.42 5.09 0.508.77 7.51 9.86 0.63 27.99 6.58 32.87 0.92The data indicate the superior performance of the ink of Example XVcompared to the ink containing the ink of Comparative Example A.Diffusion through the paper was virtually stopped. The difference becameclear after 2 days during the room temperature test and within the first24 hours during the 60° C. test.

Print Performance: Colorant Diffusion into Ink Carrier

Another disadvantage of some magenta colorants is their tendency todiffuse relatively quickly from their ink pixels into neighboring pixelson the front side of prints. This process can lead to undesirablediscoloration effects over a period of time. The inks prepared inExample XV and Comparative Example A were each incorporated intodifferent reservoirs of the printhead of a XEROX® PHASER® 850 phasechange ink jet printer. Into a third reservoir was incorporated thephase change ink carrier described in Example I. Solid fill prints weregenerated on HAMMERMILL LASERPRINT® paper with both inks by ditheringduring printing with the colorless phase change ink carrier at astandard resolution of 355×464 dpi and at 20%, 50% and 80% ink coverage.Shortly after printing, the front (printed) sides of the printed paperswere scanned with an ACS Photometer, and the respective L*a*b*coordinates were recorded. Thereafter, some of the prints weremaintained at room temperature and some of the prints were maintained at60° C. In defined time intervals of approximately 1 day, 3 days, 5 days,10 days, and 30 days as indicated in the tables, the same sites on thefront sides of the printed papers were again scanned for their colorvalues, and decolorations were quantified by calculating the ΔE valueswith respect to the initial scan. Low ΔE values are desirable. Theresults were as follows:

a) Room Temperature

Comparative Example A Example XV Time (Days) ΔE Time (Days) □E 20% InkCoverage 0.00 0.00 0.00 0.00 0.27 0.38 0.76 0.13 1.05 1.22 2.8 0.26 3.341.83 4.82 0.30 6.26 2.30 9.74 0.31 10.04 2.75 32.75 0.57 30.18 3.29 50%Ink Coverage 0.00 0.00 0.00 0.00 0.27 1.09 0.76 0.16 1.05 1.95 2.8 0.253.34 2.88 4.82 0.35 6.26 3.33 9.74 0.35 10.04 4.08 32.75 0.67 30.18 4.9980% Ink Coverage 0.00 0.00 0.00 0.00 0.27 0.80 0.76 0.23 1.05 1.46 2.80.34 3.34 2.04 4.82 0.39 6.26 1.86 9.74 0.46 10.04 2.31 32.75 0.78 30.182.54b) 60° C.

Comparative Example A Example XV Time (Days) ΔE Time (Days) □E 20% InkCoverage 0.00 0.00 0.00 0.00 0.35 5.86 0.76 0.33 1.05 8.44 2.80 0.762.04 8.50 4.82 1.06 3.04 8.25 9.74 1.33 5.13 8.24 32.75 1.46 10.06 8.0036.20 7.75 50% Ink Coverage 0.00 0.00 0.00 0.00 0.35 5.25 0.76 1.93 1.055.82 2.80 2.33 2.04 5.63 4.82 2.56 3.04 5.68 9.74 3.06 5.13 5.34 32.754.38 10.06 5.39 36.20 5.40 80% Ink Coverage 0.00 0.00 0.00 0.00 0.353.30 0.76 4.09 1.05 4.46 2.80 4.88 2.04 4.42 4.82 5.32 3.04 4.39 9.746.13 5.13 4.04 32.75 8.00 10.06 3.92 36.20 3.45As the data indicate, at room temperature, the ink prepared in ExampleXV exhibited superior performance at all degrees of ink coverage. Thediffusion of dye was minimal and was equal to zero within the errorlimits of the instrument. The difference became clear after the first 24hours. At 60° C., the ink prepared in Example XV exhibited superiorperformance at 20% and 50% ink coverage, although not at 80% coverage.

Print Performance: Fingerprint Diffusion

The inks prepared in Example XV and Comparative Example A were eachincorporated into different reservoirs of the printhead of a XEROX®PHASER® 850 phase change ink jet printer and used to generate solid fillprints onto HAMMERMILL LASERPRINT® paper. Resolutions of 355×464 dpi and600×600 dpi were applied. Horizontal solid-fill stripes of different inkfill were generated, varying from 20% fill to 90% fill in 10%increments. Fingerprint diffusion tests were then carried out on theprints by having a test person rub fingers two times with fragrance-freeLUBRIDERM® hand lotion. After each rub, the fingers were dried with atowel. The surfaces of the prints were then contaminated by touchingthem with the fingers, exerting an equal and moderate pressure.Thereafter, the prints were placed into manila folders with sheets ofpaper between the samples and maintained at room temperature for fivedays, after which the prints were inspected for changes. Fingerprintsappeared quickly in the prints generated with the ink prepared inComparative Example A, but were almost not visible in the printsgenerated with the ink prepared in Example XV. To characterize thisresult in numbers, a comparative qualitative scale, ranging from −3.0 to+3.0, was established. On this scale, the reference from ComparativeExample A was assigned a value of ±0.0. Negative values representedundesirable performance and positive values represented desirableperformance superior to the reference. The prints generated with the inkof Example XV were subjectively rated +1.5 for the prints at 355×464 dpiresolution and +2.0 for the prints at 600×600 dpi resolution. Theseratings reflect the total impression, gained from all coverages between20% and 90%, for the same resolution. The samples were then stored in adark place at room temperature for 2¼ years. After this time period, thesamples were inspected again, and it was noted that the prints fromExample XV still appeared fresh and unaltered, with almost nofingerprints visible. In contrast, the reference showed a significantamount of fading dye and a speckled appearance of the surface,indicating the presence of a degrading processes.

Other embodiments and modifications may occur to those of ordinary skillin the art subsequent to a review of the information presented herein,these embodiments and modifications, as well as equivalents thereof, arealso included within the scope of this invention.

The recited order of processing elements or sequences, or the use ofnumbers, letters, or other designations therefor, is not intended tolimit a claimed process to any order except as specified in the claimitself.

1. A compound (a) of the formula

wherein R₁ is (i) a hydrogen atom, (ii) an alkyl group, includinglinear, branched, saturated, unsaturated, cyclic, substituted, andunsubstituted alkyl groups, and wherein hetero atoms either may or maynot be present in the alkyl group, (iii) an aryl group, includingsubstituted and unsubstituted aryl groups, and wherein hetero atomseither may or may not be present in the aryl group, (iv) an arylalkylgroup, including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms either may or may not be present in either the arylor the alkyl portion of the arylalkyl group, or (v) an alkylaryl group,including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group, R₂ is a nitrile group, R₃ is (i) analkyl group, including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atomseither may or may not be present in the alkyl group, (ii) an aryl group,including substituted and unsubstituted aryl groups, and wherein heteroatoms either may or may not be present in the aryl group, (iii) anarylalkyl group, including substituted and unsubstituted arylalkylgroups, and wherein hetero atoms either may or may not be present ineither the aryl or the alkyl portion of the arylalkyl group, (iv) analkylaryl group, including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms either may or may not be present ineither the alkyl or the aryl portion of the alkylaryl group, or (v) asubstituent selected from hydroxy groups, halogen atoms, amine groups,imine groups, ammonium groups, cyano groups, pyridine groups, pyridiniumgroups, ether groups, aldehyde groups, ketone groups, ester groups,amide groups, carbonyl groups, thiocarbonyl groups, sulfate groups,sulfonate groups, sulfide groups, sulfoxide groups, phosphine groups,phosphonium groups, phosphate groups, nitrile groups, mercapto groups,nitro groups, nitroso groups, sulfone groups, acyl groups, acidanhydride groups, azide groups, azo groups, cyanato groups, isocyanatogroups, thiocyanato groups, isothiocyanato groups, carboxylate groups,carboxylic acid groups, urethane groups, urea groups, or mixturesthereof, wherein two or more substituents can be joined together to forma ring, m is an integer of 0, 1, 2, 3, or 4, R₄ is (i) an alkyl group,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkyl groups, and wherein hetero atoms either may ormay not be present in the alkyl group, (ii) an aryl group, includingsubstituted and unsubstituted aryl groups, and wherein hetero atomseither may or may not be present in the aryl group, (iii) an arylalkylgroup, including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms either may or may not be present in either the arylor the alkyl portion of the arylalkyl group, (iv) an alkylaryl group,including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group, or (v) a substituent selected fromhydroxy groups, halogen atoms, amine groups, imine groups, ammoniumgroups, cyano groups, pyridine groups, pyridinium groups, ether groups,aldehyde groups, ketone groups, ester groups, amide groups, carbonylgroups, thiocarbonyl groups, sulfate groups, sulfonate groups, sulfidegroups, sulfoxide groups, phosphine groups, phosphonium groups,phosphate groups, nitrile groups, mercapto groups, nitro groups, nitrosogroups, sulfone groups, acyl groups, acid anhydride groups, azidegroups, azo groups, cyanato groups, isocyanato groups, thiocyanatogroups, isothiocyanato groups, carboxylate groups, carboxylic acidgroups, urethane groups, urea groups, or mixtures thereof, wherein twoor more substituents can be joined together to form a ring, n is aninteger of 0, 1, 2, 3, or 4, R₅ is (i) an alkyl group, including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms either may or may not be presentin the alkyl group, (ii) an aryl group, including substituted andunsubstituted aryl groups, and wherein hetero atoms either may or maynot be present in the aryl group, (iii) an arylalkyl group, includingsubstituted and unsubstituted arylalkyl groups, and wherein hetero atomseither may or may not be present in either the aryl or the alkyl portionof the arylalkyl group, (iv) an alkylaryl group, including substitutedand unsubstituted alkylaryl groups, and wherein hetero atoms either mayor may not be present in either the alkyl or the aryl portion of thealkylaryl group, or (v) a substituent selected from hydroxy groups,halogen atoms, amine groups, imine groups, ammonium groups, cyanogroups, pyridine groups, pyridinium groups, ether groups, aldehydegroups, ketone groups, ester groups, amide groups, carbonyl groups,thiocarbonyl groups, sulfate groups, sulfonate groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, or mixtures thereof, wherein two or moresubstituents can be joined together to form a ring, p is an integer of0, 1, 2, 3, or 4, R₆ is (i) a direct bond, (ii) an alkylene group,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkylene groups, and wherein hetero atoms either mayor may not be present in the alkylene group, (iii) an arylene group,including unsubstituted and substituted arylene groups, and whereinhetero atoms are not present in the arylene group, (iv) an arylalkylenegroup, including unsubstituted and substituted arylalkylene groups, andwherein hetero atoms are not present in the aryl portions of thearylalkylene group and either may or may not be present in the alkylportions of the arylalkylene group, or (v) an alkylarylene group,including unsubstituted and substituted alkylarylene groups, and whereinhetero atoms are not present in the aryl portions of the alkylarylenegroup and may or may not be present in the alkyl portions of thealkylarylene group, G is (1) an alkyl group having at least about 17carbon atoms, including linear, branched, saturated, unsaturated,cyclic, substituted, and unsubstituted alkyl groups, and wherein heteroatoms either may or may not be present in the alkyl group, (2) an arylgroup having at least about 17 carbon atoms, including substituted andunsubstituted aryl groups, and wherein hetero atoms are not present inthe aryl group, (3) an arylalkyl group having at least about 17 carbonatoms, including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms are not present in the aryl portions of thearylalkyl group and either may or may not be present in the alkylportions of the arylalkyl group, (4) an alkylaryl group having at leastabout 17 carbon atoms, including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms either may or may not be present ineither the alkyl portions of the alkylaryl group and are not present inthe aryl portions of the alkylaryl group, (5) a group of the formula<CWU-Call

(6) a group of the formula

(7) a group of the formula

or (8) a group of the formula

R₇ is (i) an alkyl group having at least about 17 carbon atoms,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkyl groups, and wherein hetero atoms either may ormay not be present in the alkyl group, (ii) an aryl group having atleast about 17 carbon atoms, including substituted and unsubstitutedaryl groups, and wherein hetero atoms are not present in the aryl group,(iii) an arylalkyl group having at least about 17 carbon atoms,including substituted and unsubstituted arylalkyl groups, and whereinhetero atoms are not present in aryl portions of the arylalkyl group andeither may or may not be present in the alkyl portions of the arylalkylgroup, or (iv) an alkylaryl group having at least about 17 carbon atoms,including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms either may or may not be present in either the alkylportions of the alkylaryl group and are not present in the aryl portionsof the alkylaryl group, R₈ is (i) a hydrogen atom, (ii) an alkyl group,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkyl groups, and wherein hetero atoms either may ormay not be present in the alkyl group, (iii) an aryl group, includingsubstituted and unsubstituted aryl groups, and wherein hetero atoms arenot present in the aryl group, (iv) an arylalkyl group, includingsubstituted and unsubstituted arylalkyl groups, and wherein hetero atomsare not present in the aryl portions of the arylalkyl group and eithermay or may not be present in the alkyl portions of the arylalkyl group,or (v) an alkylaryl group, including substituted and unsubstitutedalkylaryl groups, and wherein hetero atoms either may or may not bepresent in either the alkyl portions of the alkylaryl groups and are notpresent in the aryl portions of the alkylaryl group, X is —O— or —NR₉—,and R₉ is (i) a hydrogen atom, (ii) an alkyl group, including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms either may or may not be presentin the alkyl group, (iii) an aryl group, including substituted andunsubstituted aryl groups, and wherein hetero atoms are not present inthe aryl group, (iv) an arylalkyl group, including substituted andunsubstituted arylalkyl groups, and wherein hetero atoms are not presentin the aryl portions of the arylalkyl group and either may or may not bepresent in the alkyl portions of the arylalkyl group, or (v) analkylaryl group, including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms either may or may not be present ineither the alkyl and are not present in the aryl portions of thealkylaryl group; or (b) of the formula

wherein R₁ is (i) a hydrogen atom, (ii) an alkyl group, includinglinear, branched, saturated, unsaturated, cyclic, substituted, andunsubstituted alkyl groups, and wherein hetero atoms either may or maynot be present in the alkyl group, (iii) an aryl group, includingsubstituted and unsubstituted aryl groups, and wherein hetero atomseither may or may not be present in the aryl group, (iv) an arylalkylgroup, including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms either may or may not be present in either the arylor the alkyl portion of the arylalkyl group, or (v) an alkylaryl group,including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms either may or may not be present in either the alkyl or thearyl portion of the alkylaryl group, R₂ is (i) a hydrogen atom, (ii) analkyl group, including linear, branched, saturated, unsaturated, cyclic,substituted, and unsubstituted alkyl groups, and wherein hetero atomseither may or may not be present in the alkyl group, (iii) an arylgroup, including substituted and unsubstituted aryl groups, and whereinhetero atoms either may or may not be present in the aryl group, (iv) anarylalkyl group, including substituted and unsubstituted arylalkylgroups, and wherein hetero atoms either may or may not be present ineither the aryl or the alkyl portion of the arylalkyl group, (v) analkylaryl group, including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms either may or may not be present ineither the alkyl or the aryl portion of the alkylaryl group, or (vi) asubstituent selected from hydroxy groups, halogen atoms, amine groups,imine groups, ammonium groups, cyano groups, pyridine groups, pyridiniumgroups, ether groups, aldehyde groups, ketone groups, ester groups,amide groups, carbonyl groups, thiocarbonyl groups, sulfate groups,sulfonate groups, sulfide groups, sulfoxide groups, phosphine groups,phosphonium groups, phosphate groups, nitrile groups, mercapto groups,nitro groups, nitroso groups, sulfone groups, acyl groups, acidanhydride groups, azide groups, azo groups, cyanato groups, isocyanatogroups, thiocyanato groups, isothiocyanato groups, carboxylate groups,carboxylic acid groups, urethane groups, urea groups, or mixturesthereof, wherein two or more substituents can be joined together to forma ring, R₃ is (i) an alkyl group, including linear, branched, saturated,unsaturated, cyclic, substituted, and unsubstituted alkyl groups, andwherein hetero atoms either may or may not be present in the alkylgroup, (ii) an aryl group, including substituted and unsubstituted arylgroups, and wherein hetero atoms either may or may not be present in thearyl group, (iii) an arylalkyl group, including substituted andunsubstituted arylalkyl groups, and wherein hetero atoms either may ormay not be present in either the aryl or the alkyl portion of thearylalkyl group, (iv) an alkylaryl group, including substituted andunsubstituted alkylaryl groups, and wherein hetero atoms either may ormay not be present in either the alkyl or the aryl portion of thealkylaryl group, or (v) a substituent selected from hydroxy groups,halogen atoms, amine groups, imine groups, ammonium groups, cyanogroups, pyridine groups, pyridinium groups, ether groups, aldehydegroups, ketone groups, ester groups, amide groups, carbonyl groups,thiocarbonyl groups, sulfate groups, sulfonate groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, or mixtures thereof, wherein two or moresubstituents can be joined together to form a ring, m is an integer of0, 1, 2, 3, or 4, R₄ is (i) an alkyl group, including linear, branched,saturated, unsaturated, cyclic, substituted, and unsubstituted alkylgroups, and wherein hetero atoms either may or may not be present in thealkyl group, (ii) an aryl group, including substituted and unsubstitutedaryl groups, and wherein hetero atoms either may or may not be presentin the aryl group, (iii) an arylalkyl group, including substituted andunsubstituted arylalkyl groups, and wherein hetero atoms either may ormay not be present in either the aryl or the alkyl portion of thearylalkyl group, (iv) an alkylaryl group, including substituted andunsubstituted alkylaryl groups, and wherein hetero atoms either may ormay not be present in either the alkyl or the aryl portion of thealkylaryl group, or (v) a substituent selected from hydroxy groups,halogen atoms, amine groups, imine groups, ammonium groups, cyanogroups, pyridine groups, pyridinium groups, ether groups, aldehydegroups, ketone groups, ester groups, amide groups, carbonyl groups,thiocarbonyl groups, sulfate groups, sulfonate groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, or mixtures thereof, wherein two or moresubstituents can be joined together to form a ring, n is an integer of0, 1, 2, 3, or 4, R₅ is (i) an alkyl group, including linear, branched,saturated, unsaturated, cyclic, substituted, and unsubstituted alkylgroups, and wherein hetero atoms either may or may not be present in thealkyl group, (ii) an aryl group, including substituted and unsubstitutedaryl groups, and wherein hetero atoms either may or may not be presentin the aryl group, (iii) an arylalkyl group, including substituted andunsubstituted arylalkyl groups, and wherein hetero atoms either may ormay not be present in either the aryl or the alkyl portion of thearylalkyl group, (iv) an alkylaryl group, including substituted andunsubstituted alkylaryl groups, and wherein hetero atoms either may ormay not be present in either the alkyl or the aryl portion of thealkylaryl group, or (v) a substituent selected from hydroxy groups,halogen atoms, amine groups, imine groups, ammonium groups, cyanogroups, pyridine groups, pyridinium groups, ether groups, aldehydegroups, ketone groups, ester groups, amide groups, carbonyl groups,thiocarbonyl groups, sulfate groups, sulfonate groups, sulfide groups,sulfoxide groups, phosphine groups, phosphonium groups, phosphategroups, nitrile groups, mercapto groups, nitro groups, nitroso groups,sulfone groups, acyl groups, acid anhydride groups, azide groups, azogroups, cyanato groups, isocyanato groups, thiocyanato groups,isothiocyanato groups, carboxylate groups, carboxylic acid groups,urethane groups, urea groups, or mixtures thereof, wherein two or moresubstituents can be joined together to form a ring, p is an integer of0, 1, 2, 3, or 4, R₆ is (i) a direct bond, (ii) an alkylene group,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkylene groups, and wherein hetero atoms either mayor may not be present in the alkylene group, (iii) an arylene group,including unsubstituted and substituted arylene groups, and whereinhetero atoms are not present in the arylene group, (iv) an arylalkylenegroup, including unsubstituted and substituted arylalkylene groups, andwherein hetero atoms are not present in the aryl portions of thearylalkylene group and either may or may not be present in the alkylportions of the arylalkylene group, or (v) an alkylarylene group,including unsubstituted and substituted alkylarylene groups, and whereinhetero atoms are not present the aryl portions of the alkylarylene groupand either may or may not be present in the alkyl portions of thealkylarylene group, G is (1) an alkyl group having at least about 17carbon atoms, including linear, branched, saturated, unsaturated,cyclic, substituted, and unsubstituted alkyl groups, and wherein heteroatoms either may or may not be present in the alkyl group, (2) an arylgroup having at least about 17 carbon atoms, including substituted andunsubstituted aryl groups, and wherein hetero atoms are not present inthe aryl group, (3) an arylalkyl group having at least about 17 carbonatoms, including substituted and unsubstituted arylalkyl groups, andwherein hetero atoms are not present in the aryl portions of thearylalkyl group and either may or may not be present in the alkylportion of the arylalkyl group, (4) an alkylaryl group having at leastabout 17 carbon atoms, including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms either may or may not be present in thealkyl portion of the alkylaryl group and are not present in the arylportion of the alkylaryl group, (6) a group of the formula

(7) a group of the formula

(8) a group of the formula

or (9) a group of the formula

R₇ is (i) an alkyl group having at least about 17 carbon atoms,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkyl groups, and wherein hetero atoms either may ormay not be present in the alkyl group, (ii) an aryl group having atleast about 17 carbon atoms, including substituted and unsubstitutedaryl groups, and wherein hetero atoms are not present in the aryl group,(iii) an arylalkyl group having at least about 17 carbon atoms,including substituted and unsubstituted arylalkyl groups, and whereinhetero atoms are not present in the aryl portions of the arylalkyl groupand either are or are not present in the alkyl portions of the arylalkylgroup, or (iv) an alkylaryl group having at least about 17 carbon atoms,including substituted and unsubstituted alkylaryl groups, and whereinhetero atoms either may or may not be present in the alkyl portion ofthe alkylaryl group and are not present in the aryl portions of thealkylaryl group, R₈ is (i) a hydrogen atom, (ii) an alkyl group,including linear, branched, saturated, unsaturated, cyclic, substituted,and unsubstituted alkyl groups, and wherein hetero atoms either may ormay not be present in the alkyl group, (iii) an aryl group, includingsubstituted and unsubstituted aryl groups, and wherein hetero atoms arenot present in the aryl group, (iv) an arylalkyl group, includingsubstituted and unsubstituted arylalkyl groups, and wherein hetero atomsare not present in the aryl portions of the arylalkyl group and eitherare or are not present in the alkyl portions of the arylalkyl group, or(v) an alkylaryl group, including substituted and unsubstitutedalkylaryl groups, and wherein hetero atoms either may or may not bepresent in either the alkyl portions of the alkylaryl group and are notpresent in the aryl portions of the alkylaryl group, X is —O— or —NR₉—,and R₉ is (i) a hydrogen atom, (ii) an alkyl group, including linear,branched, saturated, unsaturated, cyclic, substituted, and unsubstitutedalkyl groups, and wherein hetero atoms either may or may not be presentin the alkyl group, (iii) an aryl group, including substituted andunsubstituted aryl groups, and wherein hetero atoms are not present inthe aryl group, (iv) an arylalkyl group, including substituted andunsubstituted arylalkyl groups, and wherein hetero atoms are not presentin the aryl portion of the arylalkyl group and either are or are notpresent in the alkyl portions of the arylalkyl group, or (v) analkylaryl group, including substituted and unsubstituted alkylarylgroups, and wherein hetero atoms either may or may not be present in thealkyl portions of the alkylaryl group and are not present in the arylportions of the alkylaryl group.
 2. A compound according to claim 1wherein the compound is of the formula

wherein R₂ is a nitrile group.
 3. A compound according to claim 1wherein the compound is of the formula

wherein R₂ is (i) a hydrogen atom, (ii) an alkyl group, (iii) an arylgroup, (iv) an arylalkyl group, (v) an alkylaryl group, or (vi) asubstituent other than an alkyl, aryl, arylalkyl, alkylaryl, or nitrilegroup.
 4. A compound according to claim 1 wherein R₁ is a methyl group,R₂ is a hydrogen atom, m, n, and p are all 0, R₆ is —CH₂— or —CH₂CH₂—,and G is a group of the formula

a group of the formula

a group of the formula

or a group of the formula


5. A compound according to claim 1 wherein R₆ is a direct bond.
 6. Acompound according to claim 1 wherein R₆ is an alkylene group, anarylene group, an arylalkylene group, or an alkylarylene group.
 7. Acompound according to claim 1 wherein the compound is of the formula

wherein R₂ is (i) a hydrogen atom, (ii) an alkyl group, (iii) an arylgroup, (iv) an arylalkyl group, (v) an alkylaryl group, or (vi) asubstituent selected from hydroxy groups, halogen atoms, amine groups,imine groups, ammonium groups, cyano groups, pyridine groups, pyridiniumgroups, ether groups, aldehyde groups, ketone groups, ester groups,amide groups, carbonyl groups, thiocarbonyl groups, sulfate groups,sulfonate groups, sulfide groups, sulfoxide groups, phosphine groups,phosphonium groups, phosphate groups, nitrile groups, mercapto groups,nitro groups, nitroso groups, sulfone groups, acyl groups, acidanhydride groups, azide groups, azo groups, cyanato groups, isocyanatogroups, thiocyanato groups, isothiocyanato groups, carboxylate groups,carboxylic acid groups, urethane groups, urea groups, or mixturesthereof, wherein two or more substituents can be joined together to forma ring, wherein G is an alkyl group having at least about 17 carbonatoms.
 8. A compound according to claim 1 wherein G is a group of theformula


9. A compound according to claim 8 wherein R₇ is an alkyl group havingat least about 17 carbon atoms.
 10. A compound according to claim 9wherein the compound is of the formula

wherein R₂ is (i) a hydrogen atom, (ii) an alkyl group, (iii) an arylgroup, (iv) an arylalkyl group, (v) an alkylaryl group, or (vi) asubstituent other than an alkyl, aryl, arylalkyl, alkylaryl, or nitrilegroup, wherein R₇ is an alkyl group having at least about carbon 17carbon atoms.
 11. A compound according to claim 8 wherein R₇ is anarylalkyl group having at least about 17 carbon atoms.
 12. A compoundaccording to claim 8 wherein R₇ is an alkylaryl group having at leastabout 17 carbon atoms.
 13. A compound according to claim 8 wherein R₇ isan aryl group having at least about 17 carbon atoms.
 14. A compoundaccording to claim 1 wherein G is a group of the formula—(C_(a)H_(2a)O)bR₁₀ or—(OC_(a)H_(2a))bOR₁₀ wherein a is an integer representing the number ofcarbon atoms, b is an integer representing the number of repeat units,and R₁₀ is a hydrogen atom, an alkyl group, an aryl group, an arylalkylgroup, or an alkylaryl group.
 15. A compound according to claim 1wherein G is a group of the formula


16. A compound according to claim 1 wherein G is a group of the formula


17. A compound according to claim 1 wherein G is a group of the formula


18. A compound according to claim 1 wherein G is a group of the formula

wherein X is —O—.
 19. A compound according to claim 1 wherein G is agroup of the formula

wherein X is —NR₉—.
 20. A compound according to claim 1 of the formula

wherein n represents an average number and has an average value of about47

.
 21. A compound according to claim 1, having the formula

wherein n represents an average number and has an average value of about47.